Sony's Spider-Man Universe - Timeline

Mattie's shown in a school uniform when Cassie nearly hits her with the ambulance, meaning this is still during the school time. I'd say the film takes place sometime during June 2003 due to Cassie being at least 30 (so after May 26, 2003), the barbeque shown toward the beginning (a summertime activity), the Beyoncé poster (Dangerously in Love released June 23, 2003), and school still being in session (NYC schools let out late June). There's a week time jump at some point due to Cassie's visit to the Amazon, so there's a possibility it passes over into July at some point. Something I didn't catch, but one of the girls comments about being "so sad about Martha Stewart" at one point, referring to Stewart being indicted for insider trading on June 4, 2003, which matches perfectly. Should be noted that Britney Spears' "Toxic" was first released on November 15, 2003, not quite working with June 2003, but the film already has some other infamous anachronisms such as the PSP (released in March 2005 in the US) appearing, so I don't think it's too big a deal.
I'd say August 2003 since Peter Parker was born in August, traditionally.
 
BTW when he's killing those prisoners in the Kraven trailer, you see a hockey match on TV. (Yes, TVs in prison cells. Much better prison system than here in the US' "eye for an eye / you don't deserve this" mentality, I'll say.)

I'll assume with the snow it's Siberia and hockey season in Russia is between September and February.
 

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