Bowe, easily. Not even close.

Douglas fought an ill prepared, over confident and distracted Tyson who was absolutely awful on the night. Tyson just stood straight in front of him like a statue and Douglas hit him with pretty much every punch he threw. Apart from the knockdown in round 8, Douglas had everything his own way. I imagine most top heavyweights would have beaten Tyson that night. He really was that bad.

Bowe had to dig really deep to pull it out against Holyfield using a combination of boxing and sheer guts and determination. There is no way Buster Douglas could have beaten that Riddick Bowe.