Dempsey (1927) vs Tyson (1996)

[gambler49]

I go for Dempsey TKO around 7 rounds.

[Bricks]

This Dempsey would be up against a Tyson tame and listeless for the battle in comparison to his former self of 5 years before.

[IRLangmaid25]

I am going for Jack Dempsey as well over Mike Tyson he has better technical ability ion terms of punching power and foot work than Tyson and would hit Tyson with good shots from different angles from which Tyson may find it difficult to come back from.

[Goodnight, Irene]

I go for Dempsey TKO around 7 rounds.

IMO, Dempsey beats Tyson peak-for-peak, but I had to think about this one for a bit. I think Dempsey had enough left to deal with this Tyson, but his punch resistance may've slipped at this point, so Tyson could get him early, possibly.

[HomicideHenry]

Dempsey, around the 4th or 5th rounds. These two wouldnt have let up on eachother, like Dempsey/Firpo. Its my intuition that tells me that Dempsey had a stronger constitution and would have weathered Tyson's best shots to land his own.

[lucaselrey]

Dempsey without a doubt.

[Diamond WEAPON]

I think Tyson beats Dempsey at virtually any comparable point in their respective careers. I simply think his handspeed on top of his power would've been too much for Dempsey, who showed early vulnerabilities like against Firpo, and difficulties with swifter fighters, which Mike most certainly was.