Opponent Swap: Tunney-Dempsey I & Holyfield-Tyson I

In 1926 Gene Tunney was in his absolute prime, so I figure he would beat 1996 Tyson and Holyfield, who were both clearly past their best.

Dempsey would lose to Holyfield.

Dempsey v Tyson ? I don't know. I think Dempsey had more will and mental stamina at this point, but he was badly faded probably more so than Tyson. A sloppy slug fest. I'd favour Tyson to win over 10 rounds, but in a longer contest Dempsey might outlast him.

 

Tyson and holyfield both go 2-0 here.

A sub 200 fighter has a mare against either. Far too strong and aggressive for Dempsey and tunney to survive the first 5 rounds.