Mike Tyson vs Vitali Klitschko

Vitali by late rounds stoppage.

Vitali is too big, too strong and most of all too awkward for a 5'10 fighter with t Rex arms.

 

Vitali was at one of Tyson's fights - I think it was the Orlin Norris fight - and was interviewed by one of the Showtime guys. Had Vitali and Tyson fought in the early 2000s, Vitali would've stopped him (or, more likely, Tyson would've quit). If Tyson could blast you out quickly, he was fine. If he had to eat jabs and work his way inside, no.

 

Vitali was all wrong for Tyson, he had the chin to take Tyson's best punches and the awkward style to avoid the body attacks with the power to stop Tyson.
Vitali by KO/TKO around the 8th round.

 

Tyson late KO.

 

Not too likely. Tyson always looked as though he ran out of steam in the late rounds.