Marvel Cinematic Universe Timeline

Civil War vs. Spider-Man

Vision's facts are never wrong. He's basically a computer. He was created by Tony Stark (genius), an Infinity Stone (divine power), Helen Cho (genius), and Ultron (combo of genius and Infinity Stone). He cannot be wrong.

So in CA:CW when he says, "In the eight years since..." you have to believe hardcore that it's been legit eight years since the infamous "I am Iron Man" statement was made. If IM1 takes place in 2008 that means CA:CW has to take place in 2016. That's a weak "if" in my opinion, so do whatever you want with it (do whatever you want with any of this, I'm just trying to organize a rat's nest).

According to the "8 Years Later" screen title in SM:H, if Avengers took place in 2012, SM:H takes place in 2020. Some fans (myself included) believe Avengers may have actually taken place in 2011, meaning SM:H would take place in 2019. Kevin Feige stated in 2017 that they'd clear this up by releasing an official timeline (see bibliography), to which I say GOOD LUCK WITH THAT, SIR. I will have my receipts ready in the event that you do because, ohohohohohoho.......

Back to point, Vision's never wrong. Screen titles can be wrong—they're a creative statement, not "reality"—but Vision can't be. Based on Vision's comment, SM: H has to take place eight years after IM1, not Avengers. 

Now, we already discussed in the last chapter how the "Two Months Later" screen title is bogus. SM:H cannot possibly occur two months after CA:CW. However, it's still mandatory that both movies take place in the same year because:

— Peter would spend several months texting Happy with no response, but probably not six months to a year. 

— He's still very unused to his new suit and only discovers its many capabilities when Ned hacks it for him. 

— Tony says he's fourteen and Peter corrects him saying he's fifteen. During press for CA:CW, Marvel confirmed Peter is fifteen in CA:CW (lost my source for that, sorry). 

— The Tower has been uninhabited since the Avengers moved to the new facility in 2015 in AoU. Negotiations with the new buyer have probably been ongoing since the real estate is so large and important, and it's smack dab in the middle of NYC (pricey, pricey).

— In both films the grounds of the Avengers facility are green. Likewise, Washington D.C.  in S:MH is green (which we covered in the CA:TWS chapter). Finally, Liz's miniskirt & sweater ensemble indicate the temperature in New York.

— Pepper and Tony took a "break," but are now happily back together.

BUT, if you really want to rely on SM:H's 8yr mark (and Avengers taking place in 2012), you set both CA:CW and SM:H in 2020. This makes Vision sound like an idiot, implies that the Triskelion clean-up has taken six years and counting, and the Avengers were fighting Hydra for several years before AoU. This means Tony and Pepper have been dating for ten years since the ship sailed in 2010 in IM2. Ten years. Mr. What-I-Want-When-I-Want-It does not wait ten years to propose to the love of his life. 

Final nail-in-the-coffin point: both the creators and Tom Holland officially confirmed that the little boy in IM2 is Peter Parker. 

If SM:H happens ten years after that, Peter would have been five in IM2. The child actor in that film was eight. I know actors can play characters of varying ages, especially kid actors, but an eight-year-old is not a five-year-old. Ask the director, he should know, it was his own kid.*

In conclusion, COMPLETELY DISREGARD THE DATES SET IN SPIDER-MAN: HOMECOMING. 

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*The actor was Max Favreau, Jon Favreau's oldest child.