Is Robert Downey Jr. the only actor to lay claim to working with at least 2 of the big screen Peter Parkers?
Of course this movie and Captain America: Civil War with Tom Holland and Wonder Boys and Tropic Thunder with Tobey Maguire. I'm not entirely sure, he has ever done anything with Andrew Garfield as of yet.
I suppose that JK Simmons could count based on his return cameo as J. Jonah Jameson in Spider-Man: Far From Home. This is despite the fact that he isn't actually physically in a scene with Tom Holland. Come to think of it, Jake Gyllenhaal was also in Far From Home as Mysterio after working with Tobey Maguire in Brothers.