In just over 2 weeks, Marvel Studios and Sony’s Spider-Man trilogy will conclude in Spider-Man: No Way Home. By the time it’s all said and done, Tom Holland’s iteration of Spider-Man/Peter Parker will have appeared in 6 MCU films stretching all the way back to 2016’s Captain America: Civil War; however, thanks to Amy Pascal, we now know this isn’t the end of the road for Holland as the Web-Slinger’s time in the MCU as Sony and Marvel Studios have extended their deal to collaborate on the character’s solo films. With Pascal indicating the two studios will now be working on another trilogy, its seems like a good time to look ahead and think about when we might see those new solo Spidey films in theaters.
Spider-Man 4: Fall/Winter 2023

Part of the original deal with Marvel Studios and Sony revolved around a solo Spidey film being in theaters every 2 years. This meant that Holland spent a whole lot of time in spandex from 2015 through 2020, but that’s the life of an actor! Sony is scheduled to kick of the 2023 superhero slate with Kraven the Hunter in January and Marvel Studios currently has The Marvels, Guardians of the Galaxy Vol. 3 and Ant-Man and the Wasp: Quantumania spread out from February through late-July with an as yet unannounced film on the slate for November 3rd. That won’t be Spidey 4 because Sony picks those dates, but December of 2023 is currently unclaimed by Marvel Studios, Star Wars or DC. A December 2023 date would mean Spidey 4 wouldn’t need to start filming until late 2022, giving the studio plenty of time to get a script together (if they haven’t already started) and give Holland some time to do some other work as well.
Spider-Man 5: Summer 2025

The first two MCU Spidey films hit theaters in July and 2025 provides the opportunity to do just that, assuming they keep the 2 year gap between films. Marvel Studios hasn’t announced any plans for 2025 as yet, but Lucasfilm currently has a Star Wars film on the books for December of 2025. So, back to summer it goes for Spidey 5.
Spider-Man 6: Summer 2027

It’s hard to fathom talking about a film that could take place in 2027, but here we are. Again, assuming a 2-year gap, we’re looking at Spidey 6 concluding the second trilogy in the Summer of 2027.
Of course, at this point we don’t know much at all about how this will ACTUALLY play out. According to a trade report, the deal Pascal talked about isn’t even finalized yet and as we’ve seen in the past, there’s many a slip ‘twixt the cup and the lip when it comes to these things. However, it’s sure fun to think about.