Despite GeekTyrant’s reaction to the possibility. Wouldn’t really work, anyway. Spider-Man is still Sony, even if Deadpool is Disney/Marvel now; and I cannot imagine that Ryan Reynolds and his crew are going to be willing to do the PG-13 version that Sony would expect*. And, comes right down to it: the tone would be off. On both sides. I don’t know what the hell Spider-Man would do with a Deadpool. Shoot, I don’t know what Deadpool would do with a Spider-Man, and neither would he.
Mind you, if they want to release Deadpool Rifftrax or something to MCU and Spider-verse flicks, well, I could be down with that.
*Neither side would wrong, by the way. Sony is doing well for itself by making Spider-Man movies that I could take my kids to see; and Reynolds et. al. are doing well for themselves by making hysterical R-rated Deadpool flicks. There’s no shame in the fact that there’s no overlap.