Mike Tyson '88' vs Riddick Bowe '92'

I'm going with Tyson. Bowe was a dirty fighter, and his bully and cheap shot tactics would be met with the same or worse. Tyson would wear him down and pull of a UD win. Bowe likely had a point or two deducted for fouls as this is an ugly fight.

 

Holyfield barely weighed 14 stone in their first fight & hadn't quite settled at heavyweight, which allowed Bowe to cuff him around the ring, he bulked up for the re-match & appeared physically stronger giving Bowe less of an advantage & Holyfield got the win.
I loved Bowe but he always took punches & he could not have stood in the pocket & traded with Tyson.