2) SPIDER-MAN 2099
Thanks to stupid Wolverine breaking the timestream, Miguel O’Hara traveled back from his future (technically Earth-TRN588, an alternate world that diverged from Earth-923, the world of the original 2099 universe) to the Heroic Age, interacting with the original Spider-Man and working undercover as “Michael O’Mara” and operating in his past. He ends up being killed in the year 2019, decades before he is even born.
Of course, he’s a superhero, so that’s not the end of his story.