Batman: Arkham Game Series - Timeline

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Yes I've tried to include as much as possible. You will find with almost every single franchise that its extended media is contradictory or retconned by the main material at one point or another. So unless there's an insane contradiction, all media is included.
It's not much different from Freedom Fighters: The Ray being canon to the Arrowverse, honestly.
 
Didn't they say that the King Shark in KTJL was a relative of the King Shark seen in Assault on Arkham, or am I mistaken?
Pretty sure that's a misinterpretation of Penguin referencing his pet shark. If anything, I'd accept them as the exact same character and he was just revived/regenerated off-screen. That is within his power set, after all.
 
As for Boomerang... I don't know, maybe a multiverse hopping Digger Harkness revived all his variants like that one comic with Red Mask and all the dead Jokers. This **** is normal in DC, he could have just been cloned.
 
Other things that can help you, I've read the Arkham Knight novelization and it dates some of the flashbacks and events. It says that the attack on Pauli's Diner happened the night before Arkham Knight, as the last AK comics arc says that the occupation will start on the 31st, it means that the attack happened on the 30th of October, then considering the passage of time on the clock tower, means that the totality of Arkham Knight minus the Knightfall protocol happens from the 30th of October to the 1st of November;

The flashback with Gordon at Panessa studious is dated to happen 7 days earlier, as at the time of Arkham Knight Chapter 2 it's still the 31st, this place the flashback to the 24th of October. (It's also important to note that the novel imply that the flashback isn't real and it's in Batman's head. Which makes sense as to why Gordon never specify anything out of it, as the line Gordon says to Batman in the Harley Quinn's revenge DLC, of they have smt to talk about, refears to the events of End Game. At the same time tho, if the game wanted it to be an illusion, they would have outright said so);

And finally the knightfall protocol, as the part with Mayor Gordon, is stated in the novel to take place in an unspecified day of March of the next year.

And that's all from the novel!

As for bonus stuff, the first 10 Chapters of the novels are set between the attack and the actual start of the game's event; And during the story there are chapters wich describes what Gordon is doing between his visit to the clock tower and when we meet him again at the AK HQ,
 
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So GothamPaladin made a sequel video to his Arkham Knight Video, this time with Arkham City. (It was released 4 months ago but shhh).

Since it is so old maybe I did send it already and I just forgot, in case I apologize to all for wasting your times:

https://www.youtube.com/watch?v=vrmSm_0w8cA

so, the time is a bit tricky but I want to focus on one error that he made. The Azrael side mission isn't the last piece of story that Batman does in the game, why? Cos for the people who don't like to complete games at 100% (or like me completed city at 100% 58 times), Azrael apparitions aren't random, but story linked (and actually many side-missions, like the Bane one):

Appearence #1 - While Bruce Wayne enters Arkham City for the first time and protects Jack Rider.
Appearence #2 - After saving Catwoman in the courtroom.
Appearence #3 - After leaving the steelmile.
Appearence #4 - After Interrogating Quincy Sharp.
Appearence #5 - After Saving Vicky Vale.
At this point you have all the simbols to do the map, so yeah this is the moment where you could say that Batman does it for last, but I mean, he has all the symbols right now, I don't thiink he'd wait to go there and finally talk with Azrael. Yeah, this last point is my interpretation, but Azrael ending before Batman goes to the Steelmile again seems resonable to me.

Also for Deadshot, in all my runs, I only did the Deadshot side mission, just with oracle's tips on where to find the bodies. So IDK if it's possible to find them all by yourself asap like Hush side mission.

I don't promise anything, but maybe tomorrow I'll do 4 posts each for how to make the side missions fit with every main Arkham Main Games (beside Shadows as it doesn't have side missions but just collectibles).
 
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Ok guys it's a new day, and so it's time to analise these side missions, in this first post out of 4 we'll analize Arkham Asylum, but before doing that I'll explain you how I'll do it:

1) We need to have a schematic and simple way to divide the Main Story, and that's where the official 4 game guides do exactly that, so I'll going to list all the chapters, but just by their ENDPOINT. Why? We all played these games, and we know that when one chapters end, the other one starts soon after.

2) After doing this I'll analize every side missions the game can offer, sometimes they're linked with the main story's progression, another time there are some parts of them that are linked and the rest is left ambiguous or 3rd case, it's all ambiguous. It's important to note that expecially for the 3rd case I took a lot of liberties positioning them, but since I want to be more practical, if there's even a slight option to place them I will if not I won't.

3) after analizing them I'll add them to the finished timeline that you'll have at the end of the post, but how to read them? As I said in point 1 since the chapters are one after the other, you can't go for Chapter --> Side Mission X --> Chapter. But explaining like this is complicates, let's do it with an example:

Chapter 3
Side Mission X
Chapter 4

As I said in point 1 treat the chapters point as a transition from a chapter to another, so this scheme isn't read like this: Chapter 3 --> Side Mission X --> Chapter 4, but instead you have to read it like this: Chapter 3 ends --> During chapter 4 Side Mission X happens --> Chapter 4 ends.

Having understood all of this let's start with Batman Arkham Asylum:

Batman Arkham Asylum is made of 16 chapters, so let's put them on a map:

Chapter 1 - Ends when you exit Intensive Treatment
Chapter 2 - Ends when you enter the Medical Centre
Chapter 3 - Ends when you exit the Medical Centre
Chapter 4 - Ends when you enter the Caves
Chapter 5 - Ends when you exit the Caves
Chapter 6 - Ends when you enter the Arkham Mansion
Chapter 7 - Ends when you exit the Arkham Mansion
Chapter 8 - Ends when you enter the Penitentiary
Chapter 9 - Ends when you exit the Penitentiary
Chapter 10 - Ends when you enter the Botanic Gardens
Chapter 11 - Ends when you exit the Botanic Gardens
Chapter 12 - Ends when you enter Intensive Treatment
Chapter 13 - Ends when you enter the Caverns
Chapter 14 - Ends when you exit the Caverns
Chapter 15 - Ends when you defeat Poison Ivy
Chapter 16 - Ends when you finish the game

So now we have an understanding of the main story, but before we analize the side missions we have to understand that post-story gameplay in Asylum is non-canon, which means that everything must be completed before chapter 16 ends.

Now lets analise the side missions:

1) The Riddler, even tho you can start collect his trophies etc... before he talks to you, this is still irrelevant to this scheme as we're still in chapter 1, making this side mission's canonical start be during chapter 1; after that Batman completes all the challenges at the same time as the main sotry, but when does it end? To be able to complete all the challenges, you'd have to obtain the Ultra-Batclaw, which is unlocked during Chapter 14, but you return to the wider Arkham Island in chapter 15. It's possible that Batman does a detour to pick all the remining challenges before defeating Ivy? It's possible, but Ivy is an imposing immediate threat, while Joker doesn't pressure Batman too much to join his party, so I'd say it ends during Chapter 16.

2) So now you'd think that we're over? Well yes, but I want to go wild. Rocksteady released a Joker DLC, where you play as Joker trough challenges maps, and surprisingly, the order in how they're set follows the main story, so let's track them down!

Map #1 - Set during Chapter 1, before Batman is able to punch trough the window.
Map #2 - Set before Batman enters the Medical Center, probably happening during Chapter 2.
Map #3 - Set during Chapter 5, while Batman is in the Batcave.
Map #4 - Set Before Batman enters the Arkham Mansion, so probably set during Chapter 6.
Map #5 - Set before Batman enters the Penitentiary, since Harley hid Sharp in the Penitentiary while Batman was unconcious this must take place during Chapter 7.
Map #6 - Set Before Batman enters in the Intensive Treatment, suggesting a Chapter 11 placement, but since the next map is set earlier, this must be set during Chapter 9.
Map #7 - Set after Batman gets slowed down by Joker, so during Chapter 11.
Map #8 - Set before Batman exit the Batcave, since the Killer Croc part is very long it's possible that Joker could have cleared the upper levels of the caves before Batman finished collecting the spores, placing the last map during Chapter 14.

And with that here's our final timeline:

Joker - Map #1
The Riddler - Start
Chapter 1 - Ends when you exit Intensive Treatment
Joker - Map #2
Chapter 2- Ends when you enter the Medical Centre
Chapter 3 - Ends when you exit the Medical Centre
Chapter 4 - Ends when you enter the Caves
Joker - Map #3
Chapter 5 - Ends when you exit the Caves
Joker - Map #4
Chapter 6 - Ends when you enter the Arkham Mansion
Joker - Map #5
Chapter 7 - Ends when you exit the Arkham Mansion
Chapter 8 - Ends when you enter the Penitentiary
Joker - Map #6
Chapter 9 - Ends when you exit the Penitentiary
Chapter 10 - Ends when you enter the Botanic Gardens
Joker - Map #7
Chapter 11 - Ends when you exit the Botanic Gardens
Chapter 12 - Ends when you enter Intensive Treatment
Chapter 13 - Ends when you enter the Caverns
Joker - Map #8
Chapter 14 - Ends when you exit the Caverns
Chapter 15 - Ends when you defeat Poison Ivy
The Riddler - Ends
Chapter 16 - Ends when you finish the game

And that's it from Batman Arkham Asylum, in the next post I'll analise Batman Arkham City!
 
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Also btw this is another universe timeline that Robot Chicken special can be added to. (Also I saw Nolanverse Two-Face show up in the special too but that's only relevant for another thread. I wonder if there's other pre established versions in here I'm missing)
 

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Batman Arkham City is made of 10 chapters, so let's put them on a map:

Chapter 1 - Ends when you wear your Batsuit
Chapter 2 - Ends when Catwoman exit the Tribunal
Chapter 3 - Ends when you exit the Church
Chapter 4 - Ends when you switch to Catwoman
Chapter 5 - Ends when you defeat the Penguin
Chapter 6 - Ends when you defeat Ra's al Ghul
Chapter 7 - Ends when you defeat Mr. Freeze
Chapter 8 - Ends when you switch to Catwoman
Chapter 9 - Ends when you end Protocol 10
Chapter 10 - Ends when you finish the Game

and that's for the main story, keep in mind that differently from Asylum the post-story gameplay is canon, so we have to keep this in mind, and now let's start with the side missions regarding Batman:

1) A.R. Training - This side missions falls under the 2nd case, infact canonically the mission starts while Batman is tracking Joker to the Steelmile, setting the start of it during Chapter 4, but after you acquire the Grapple Boost, he could have done the challenges at any time, maybe there's a path where you can complete it smothly with the main story, but I couldn't find any, so idk where it could end.

2) Fragile Alliance - People don't know this, but this story is actually linked with the main story and you can do it without even looking at the map how? I'll explain it to you just now:
Meeting Bane - As GothamPaladin said, Batman would definetly meet Bane while he was tracking Joker, as it is made aware thanks to a rocket signal, and it's closer to where he's going anyway, placing their meeting during Chapter 4.
The Bowery Titan Container - Batman destroys it before he enters the Metro as it is positioned close to the entrance, so during Chapter 5.
Metro Titan Container - Batman destroys it while he's disarming the Metro Jammer placing its destruction during Chapter 5.
Museum Titan Container - Batman destroys it after or shortly before freeing Mr. Freeze, so during Chapter 5.
Industrial District Container - Batman destroys it while he's tracking the ninja, as the Metro entrance is closer to its position, so during Chapter 6.
Wonder City Titan Container - Batman destroys it while he's trackiing the ninja, so during Chapter 6.
Steelmile Titan Container - Batman destroys it while he's going after the Joker to take the cure, so during Chapter 8. I know that you can destroy this earlier, but I don't see why Bruce would do it earlier.
Final Confrontation with Bane - you can definetly exit the Steelmile, finish the mission and then return for Joker, but I feel like the Tyger assaulting Bane makes way more sense, and also it's along the way trough the helicopters, so it makes sense to me to end it during Chapter 9.

3) Shot in the Dark - I usually do this side mission differently, and I don't know if what GothamPaladin does in his video is possible, but lets give him the benefit of the doubt and lets say he's right, this place this side mission during Chapter 5.

4) Acts of Violence - this side mission canonically starts as soon as you wear the Batsuit, if you go all on the right instead of going to the Tribunal, you can find Jack Rider and save him, starting this side mission, so the mission starts during Chapter 2, but it's impossible to tell when it ends thanks to its nature.

5) Remote Hideway - this side mission gets unlocked after Interrogating Quincy Sharp, so I guess it gets done right after, so during Chapter 7.

6) Cold Call Killer - This mission is too random to pinpoint a start and an ending, Infact I think that just the 1st call you can find under the bridge in Park Row it's story linked, so placing the start during Chapter 2 I think.

7) Identity Theft - This mission would surprise you, but it's actually story linked, so lets do a quick explaining:
Body #1 - Hugo reveals its position to you after you exit the Metro, so making this mission canonically start during Chapter 5.
Body #2 - You can find body 2 right after Robin gives you the Line Launcher, you just need to walk over the edge of the roof you're standing and poof you'll find the body, so during Chapter 6.
Body #3 - The body is positioned next to the Welcome Centre of Arkham City, which means that you'd be able to find it before interrogating Quincy Sharp or during Protocol 10, I feel like Batman does it during Protocol 10 as it would make more sense as to why Batman lets Hush go away, so during Chapter 9.

8) The Tea Party - This one is super easy, it mentions Batman still being infected and gets unlocked after saving Vicky Vale, placing it during Chapter 8.

9) Watcher in the Wings - I already discussed this side mission yesterday, so I'll just copy paste it:
Appearence #1 - While Bruce Wayne enters Arkham City for the first time and protects Jack Rider, so during Chapter 1.
Appearence #2 - After saving Catwoman in the courtroom, so during Chapter 3.
Appearence #3 - After leaving the steelmile, so during Chapter 5.
Appearence #4 - After Interrogating Quincy Sharp, so during Chapter 7.
Appearence #5 - After Saving Vicky Vale, so during Chapter 8.
At this point you have all the simbols to do the map, so yeah this is the moment where you could say that Batman does it for last, but I mean, he has all the symbols right now, I don't thiink he'd wait to go there and finally talk with Azrael. Yeah, this last point is my interpretation, but Azrael ending before Batman goes to the Steelmile again seems resonable to me, so it ends during chapter 8.

10) Heart of Ice - This missions canonically starts after Batman defeats Freeze, I see people thinking that Batman wouldn't loose too much time looking for her soon after and instead going to do other stuff, but Batman promised Freeze to find her, so why wouldn't do that right away? So I'm placing it during Chapter 8.

11) Hot and Cold - This mission is super easy, it is unlocked during your second visit in the Steelmile and can be completed right away, since it's super close I can see Batman doing it as soon as it is unlocked.

12) Enigma Conundrum - Finally, the Riddler's mission... as with Asylum you can start completing his challenges as soon as Chapter 2, but let's stick with the main events, the mission becomes available after leaving the GCPD to look for Freeze, during Chapter 5, there's our start! And for all the rooms? I don't have the slightest Idea, but let's talk about the ending, to complete the riddler you have to complete 400 of his challenges, so you can finish his mission way earlier if you play enough with Catwoman, but I higly doubt that Batman and Catwoman would share their trophies together, so let's focus on Batman's 400. In order to get all of them, you need to have Tyger's security codes, so it could be possible to do all the challenges when you reach Chapter 9, but Protocol 10 is in act and the Riddler isn't along the way for Batman to complete at this moment so I'd leave Riddler's end for the post-game.

And with this we finished with Batman, let's go to Catwoman:

1) Catwoman DLC - The Episodes aren't considered part of the Chapters of the main story in the official guide, so let's separate them and place them how they happens in the game (NOTE: you could argue that Episode 2 and 3 happens one after the other, but I don't want to complicate things further, so let's stick to how the game separated them)

2) The Riddler - as stated in the side mission I don't think her and Batman shared their trophies etc... and we don't know where they should start or end for Catwoman, so really up in the air.

3) Catwoman's Loot - This is super easy, it unlocks after playing Episode 4, so it must happen in the post-game.

And with that here's our final timeline:

Catwoman - Episode 1
Watcher in the Wings - Meeting Azrael #1
Chapter 1 - Ends when you wear your Batsuit
Acts of Violence - Starts but ending is unknown.
Cold Call Killer - Starts but ending is Unknown
Chapter 2 - Ends when Catwoman exit the Tribunal
Watcher in the Wings - Meeting Azrael #2
Chapter 3 - Ends when you exit the Church
Fragile Alliance - Meeting Bane
A.R. Training - Starts, when it ends is unknown
Chapter 4 - Ends when you switch to Catwoman
Catwoman - Episode 2
Watcher in the Wings - Meeting Azrael #3
Shot in the Dark - Victim #1
Enigma Conundrum - Starts
Shot in the Dark - Victim #2-3
Fragile Alliance - The Bowery, Metro Titan Containers
Identity Theft - Body #1
Fragile Alliance - Museum Titan Containers
Chapter 5 - Ends when you defeat the Penguin
Identity Theft - Body #2
Fragile Alliance - Industrial District and Wonder City Titan Containers
Chapter 6 - Ends when you defeat Ra's al Ghul
Watcher in the Wings - Meeting Azrael #4
Remote Hideway
Chapter 7 - Ends when you defeat Mr. Freeze
Watcher in the Wings - Meeting Azrael #5 and ending
The Tea Party
Heart of Ice
Fragile Alliance - Steelmile Titan Containers
Hot and Cold
Chapter 8 - Ends when you switch to Catwoman
Catwoman - Episode 3
Fragile Alliance - Final confrontation with Bane
Identity Theft - Body #3
Chapter 9 - Ends when you end Protocol 10
Chapter 10 - Ends when you finish the Game
Catwoman - Episode 4
Enigma Conundrum - Ends
Catwoman's Loot

And ta-da! Look at that we finished Batman Arkham City, in my next post I'll deal with Batman Arkham Origins!
 
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Batman Arkham Origins is made of 7 chapters, let's take a look at them:

Chapter 1 - Ends when you restore Coventry Tower
Chapter 2 - Ends when you exit the Final Offer
Chapter 3 - Ends when you resolve the Lacey Towers Murders
Chapter 4 - Ends when you exit the Steelmile
Chapter 5 - Ends when you defeat Bane
Chapter 6 - Ends when you defeat Firefly
Chapter 7 - Ends when you end the game

And that's it for the main story, and as with Arkham City, the post-game is canon in Origins, so lets dive into these side missions:

1) Anarky - This one gets unlocked after you exit the Final Offer, and since Anarky is targeting people with boms, I think it would take precedence rather than a crime scene, so it happens during Chapter 3.

2) Penguin's Arms Caches - This mission gets unlocked after leaving the GCPD, during Chapter 3, and can be completed in one go, but Barbara's dialogues with Batman feels like this missions goes for way longer, making its endpoint unknown.

3) Mad Hatter - This one is easy to place it gets unlocked after you exit the GCPD a second time, so during Chapter 4, and it gets completed in one go there, since Batman would def go after him as he has an hostage.

4) Lady Shiva - This side mission I think could be unlocked as soon as Chapter 2, but I feel like it is done in one go during Chapter 4 after you exit the Gotham Merchants Bank, as it is super close and the only way I think Batman would be able to find it, also Ik she appears in call during the Hotel meeting, I'll discuss it on our next point.

5) Deadshot - This side mission is unlocked while you're tracking Electrocutioner, so during chapter 5 and I think it gets done right away in one go. And yeah as well with Shiva, he is in call aswell, but you'd see Batman ignoring a distress call? Well, I can't so that's why I'm ingoring their appearences.

6) Bird - This side mission gets unlocked during your third visit at the GCPD, so during Chapter 6, I think Batman does it in one go, as people are fighting, so better clean that up as soon as possible and also because if you reach Bane's hideout his men will talk about Bird's mission at the My Aliby, so better do it right as it spawns in Chapter 6.

7) Black Mask - This side mission gets unlocked before you exit the steelmile, but can be attempted completition during Chapter 5. Tho I don't think Batman would start them as he has more important things to deal with, and most importantly some containers requires Electrocutioner's gauntlets for destroying them, making the end of the mission at least happening during Chapter 6, but we don't know for certainly if it gets done there.

8) Blackgate Prisoners - This is super easy as it is unlocked after every other side mission is completed along with the main story, so it happens in one go in the post-game.

9) Collectibles and Crime Scenes - putting this here cos I'd say the same thing, the Crime Scene are completely random but as explained in the previous point they must finish before the Blackgate Prisoners side mission, and for the rest, I don't have a single clue, but needs Electrocutioner's gauntlets for all of them to be done, so at least during Chapter 6.

10) Enigma - we end with him again, and as said in the previous point it's impossible to pinpoint the collectibles for when he started, but differently from the other collectibles the other activities has to offer, Batman must have been completed all Enigma's activities in the post-game, as it needs the Pioner's Bridge to be destroyed for being able to obtain the last 3 Datapacks, so we can assume that the ending occurs soon after; while for the start of it, it happens soon before Batman frees the Conventry Tower so during Chapter 1.

and with that, here's our full timeline:

Enigma - Starts
Chapter 1 - Ends when you restore Coventry Tower
Chapter 2 - Ends when you exit the Final Offer
Anarky
Penguin's Arms Caches - Starts but ending is unknown
Chapter 3 - Ends when you resolve the Lacey Towers Murders
Mad Hatter
Lady Shiva
Black Masks - starts but ending is unknown
Chapter 4 - Ends when you exit the Steelmile
Deadshot
Chapter 5 - Ends when you defeat Bane
Bird
Chapter 6 - Ends when you defeat Firefly
Chapter 7 - Ends when you end the game
Enigma - Ends
Blackgate Prisoners

And with that we finished Batman Arkham Origins, now in my 4th and last post I'll analise Batman Arkham Knight!
 
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and here we are with Batman Arkham Knight which I think will be the longest post, thanks to its very different nature, but lets start simple.

Batman Arkham Knight is made of 9 chapters, let's put them right here:

Chapter 1 - Ends when you locate Ace Chemicals
Chapter 2 - Ends when you leave Ace Chemicals
Chapter 3 - Ends when you enter the Stagg Airships
Chapter 4 - Ends when you exit the Stagg Airships
Chapter 5 - Ends when Harley takes over the Panessa Studios
Chapter 6 - Ends when you upgrade the Batmobile
Chapter 7 - Ends when Gordon contacts the GCPD
Chapter 8 - Ends when you enter the GCPD
Chapter 9 - Ends when you end the game

The guide considers the Knightfall Protocol as part of Chapter 9, meaning that technically like in Asylum the post-game gameplay is non-canon.

now before going into the side missions we have to understand how do they work in this game, basically the main mission breaks to give you time to do the side missions, my analisis assumes that during these breaks Batman advances in all of the side missions he has available. The side missions have also breaks and those will be used to determine when Batman switch to another activity.

so before analising the side missions we have to uncover all these breaks and when do they happen:

1st Break - During Chapter 1, after Batman delivers Poison Ivy to the GCPD.
2nd Break - During Chapter 3, after Batman exits the Orphanage.
3rd Break - During Chapter 3, After Batman investigates the crime scene.
4th Break - During Chapter 3, After Batman gives the Batmobile its first upgrade.
5th Break - During Chapter 5, After Batman delivers Poison Ivy to her plants.
6th Break - During Chapter 5, After Batman defends Poison Ivy.
7th Break - During Chapter 5, After Batman gets the Batmobile on Founder's Island.
8th Break - During Chapter 7, After Batman upgrades the Batmobile.
9th Break - During Chapter 7, After Poison Ivy dies.
10th Break - During Chapter 9, After Batman protects Oracle's servers.
11th Break - During Chapter 9, After you exit the Panessa Studios.

And with that we know when every break happens, now we'll analise and work on all the side missions with the breaks, and then we'll add them to the timeline with the main game. So lets finally analise all these side missions:

1) VR Training - The VR missions are canon in these game, they have actually a position in the chapters, unfortunaly I can't seem to access the guide from the internet archive atm, but just watch the requirement and do they when they become available.

2) The Line of Duty - This is one of the rare missions where I don't think the breaks will help us much, what we know is that canonically it starts during Chapter 1, but we don't know where it ends aside from at least post-Chapter 5, as Batman gets the Batmobile on Founder's Island.

3) The Perfect Crime - Another rare case, and the resonings are actually the same as the point above.

4) Creature of the Night - we can divide this mission just fine:
Man-Bat is spotted - After Batman exits the Clock Tower, so during Chapter 1.
First Encounter - After Batman lowers the Mercy Bridge, so during Chapter 3.
Langstrom's Lab - Soon after First Encounter, so during Chapter 3.
Second Encounter - After Oracle's death, so during Chapter 5.
Third Encounter - After Batman defeats Harley Quinn, so during Chapter 7.

5) Friend in Need - This side mission gets unlocked in Chapter 8 after Batman upgrades the Batmobile.

6) Gotham on Fire - This mission can be played linked with the main story:
Bristol Firehouse - Unlocked after the crime scene investigation, so during Chapter 3.
Cauldron Firehouse - Unlocked after Firefly's first encounter but needs time to appear, so I assume is done in the next break, so during Chapter 3.
Otisburg Firehouse - Unlocked after lowering Founder's Island bridge, so during Chapter 5.

7) Heir to the Cowl - Another mission where you don't have a clear path, the only thing we have is the start of the mission which happens during Chapter 3, the rest is unknown.

8) Two-Faced Bandit - This mission is interesting, this one doesn't have breaks meaning that Batman must have done it in one go, tho it gents unlocked after you deliver Ivy to the plants, in a time where the Batmobile can't reach Founder's Island, meaning that it has to happen during the 7th Break.

9) Lamb to the Slaughter - easy mission, it's done in one go and it's unlocked during Chapter 9, before the 10th Break, so probably Batman does it during that break.

10) Gunrunner - This mission is easy too put as it's not even Batman who searches for Penguin's Vault, but it's Nightwing that calls him:
Weapon Cash #1 - Part of Chapter 3.
Weapon Cash #2 - After bringing Ivy to her Plants, so during Chapter 5.
Weapon Cash #3 - It's Unlocked after the Batmobille is on Founder's Island, so during Chapter 5.
Weapon Cash #4 - It's unlocked after you upgrade the Batmobile, so during Chapter 7.
Weapon Cash #5 - Batman goes to save Nightwing soon after the last deposit, so Chapter 7.
This means that the Penguin gets defeated before Batman gets unmasked, people say that this can't be possible, tho they forget that Bruce wants to spend the rest of his life in a cell after he defeats Scarecrow.

11) Own the Road - This side mission can be unlocked just before the 5th break, but it's impossible to state where it ends.

12) Occupy Gotham - Same exact thing as the previous point.

13) Armored and Dangerous - So while the side mission does have a clear path, if you do 1 progression for each break, you'll be out of 1... so yeah the ending is unknown.

14) Campaign for Disarmament - This mission doesn't have a clear path, but we can pinpoint a beginning and an ending, so the beginning occurs during the main mission, so during Chapter 3, for the ending since I want to have the Scarecrow be the last one Batman captures (as Cash says that is his best gift yet), and thanks to the progression of the bombs of the map, this mission must end during Break #11, so during Chapter 9, to explain why Craine doesn't have the Militia with him anymore. So this means that regarding the 4 preceding points all those missions has to finish somewhere between their introduction and Chapter 9.

15) Riddler's Revenge - It's finally time for him!!! THE RIDDLER! it actually has a path, as for the collectibles, I've just assumed that Batman does them while he does the main story and side missions, anyways let's see how it's done:
Riddler Challenge #1 - You can complete this during Break #1, so during Chapter 1.
Riddler Challenge #2 - It's unlocked after you meet Catwoman at the Orphanage, so during Break #2, in Chapter 3.
Riddler Challenge #3 - The mission doesn't stop after the previous challenge so we're still in Break #2, in Chapter 3.
Riddler Challenge #4 - The challenge would be completed on Break #3, during Chapter 3.
Riddler Challenge #5 - With this Challenge we're in Break #4, during Chapter 3.
Riddler Challenge #6 - The mission doesn't stop, so you doing it soon after the previous one, so we're still in Break #4, in Chapter 3.
Riddler Challenge #7 - We have to move this mission later as it is set on Founder's Island, so we're now in Break #7, in Chapter 5.
Riddler Challenge #8 - This challenge would be completed on Break #8, in Chapter 7.
Riddler Challenge #9 - This challenge would be completed on Break #9, in Chapter 7.
Riddler Challenge #10 - This Challenge would be completed on Break #10, in Chapter 9.
Riddler Robot - This happens soon after you finish the 10th Challenge, so we're still on Break #10, in Chapter 9.
Riddler Boss Fight - Arrived at this point you should have collected everything, so you could go inside again and fight Riddler, so we're still in break #10, in chapter 9.

And those were all the side missions, but it isn't over! The Season of Infamy exist, which are side missions reported to Batman, so they must be done as soon as possible, so let's take a look at those side missions aswell:

1) Beneath the Surface - This side mission doesn't have stops and it's unlocked before Break #5, so in Chapter 5

2) Shadow War - This mission doesn't have stops and it's unlocked before Break #3, so in Chapter 3. This also means that canonically Batman obtains the REC during Chapter 3 (even tho I like to obtain it as soon as I get to the GCPD first time).

3) In from the Cold - This mission doesn't have stops and it's unlocked before Break #8, so in Chapter 7.

4) Wonderland - The only side mission in the Season of Infamy that has stops, so let's see them:
Hostage #1 - The mission gets unlocked before Break #2, so in Chapter 3.
Hostage #2 - Batman must have saved this hostage during Break #3, so in Chapter 3.
Hostage #3 - Batman must have saved this hostage during Break #4, so in Chapter #3.
Ending - There are no stops here so we're still in Break #4, Chapter 3.

so now let's put all the side missions in the 11 breaks:

1st Break - Riddler's Revenge (Riddler Challenge #1), The Perfect Crime (Stars, but ending is unknown), The Line of Duty (starts, but ending is unknown), Creature of the Night (Man-Bat is spotted)
2nd Break - Campaign for Disarmament (Starts), Riddler's Revenge (Riddler's Challenge #2-3), Creature of the Night (First Encounter & Langstrom's Lab), Wonderland (Hostage #1)
3rd Break - Gotham on Fire (Bristol Firehouse), Riddler's Revenge (Riddler Challenge #4), Heir to the Cowl (Starts, but ending is unknown), Wonderland (Hostage #2), Shadow War
4th Break - Gotham on Fire (Cauldron Firehouse), Riddler's Revenge (Riddler Challenge #5-6), Gunrunner (Weapon Cash #1), Armored and Dangerous (Starts, but ending is unknown), Wonderland (Hostage #3 and Ending)
5th Break - Gunrunner (Weapon Cash #2), Occupy Gotham (Starts, but ending is unknown), Creature of the Night (Second Encounter), Own the Road (Starts, but ending is unknown), Beneath the Surface
6th Break -
7th Break - Gotham on Fire (Otisburg Firehouse), Gunrunner (Weapon Cash #3), Riddler's Revenge (Riddler Challenge #7), Two-Faced Bandit
8th Break - Gunrunner (Weapon Cash #4-5), Riddler's Revenge (Challenge #8), A Friend in Need, Creature of the Night (Third Encounter), In from the Cold
9th Break - Riddler's Revenge (Riddler Challenge #9)
10th Break - Lamb of the Slaughter, Riddler's Revenge (Riddler's Challenge #10 to Riddler Boss Fight)
11th Break - Campaign for Disarmament (Ends)

Now let's combine the Main missions and side missions in a single timeline:

Riddler's Revenge - Riddler Challenge #1
The Perfect Crime - Stars, but ending is unknown
The Line of Duty - starts, but ending is unknown
Creature of the Night - Man-Bat is spotted
Chapter 1 - Ends when you locate Ace Chemicals
Chapter 2 - Ends when you leave Ace Chemicals
Campaign for Disarmament - Starts
Riddler's Revenge - Riddler's Challenge #2-3
Creature of the Night - First Encounter & Langstrom's Lab
Wonderland - Hostage #1
Gotham on Fire - Bristol Firehouse
Riddler's Revenge - Riddler Challenge #4
Heir to the Cowl - Starts, but ending is unknown
Wonderland - Hostage #2
Shadow War
Gotham on Fire - Cauldron Firehouse
Riddler's Revenge - Riddler Challenge #5-6
Gunrunner - Weapon Cash #1
Armored and Dangerous - Starts, but ending is unknown
Wonderland - Hostage #3 and Ending
Chapter 3 - Ends when you enter the Stagg Airships
Chapter 4 - Ends when you exit the Stagg Airships
Gunrunner - Weapon Cash #2
Occupy Gotham - Starts, but ending is unknown
Creature of the Night - Second Encounter
Own the Road - Starts, but ending is unknown
Beneath the Surface
Gotham on Fire - Otisburg Firehouse
Gunrunner - Weapon Cash #3
Riddler's Revenge - Riddler Challenge #7
Two-Faced Bandit
Chapter 5 - Ends when Harley takes over the Panessa Studios
Chapter 6 - Ends when you upgrade the Batmobile
Weapon Cash #4-5
Riddler's Revenge - Challenge #8
A Friend in Need
Creature of the Night - Third Encounter
In from the Cold
Riddler's Revenge - Riddler Challenge #9
Chapter 7 - Ends when Gordon contacts the GCPD
Chapter 8 - Ends when you enter the GCPD
Lamb of the Slaughter
Riddler's Revenge - Riddler's Challenge #10 to Riddler Boss Fight
Campaign for Disarmament - Ends
Chapter 9 - Ends when you end the game

And with this I finish this analisis of the side missions of the Arkhamverse, I hope it was helpful!
 

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