Wills by KO probably. That's the fight where I like Wills' chances against modern-day HW Maskaev was skilled enough, but slower than turtle, and possessed a glass jaw
But he did beat Rahman twice. Rahman was very strong and powerful, don't know if he landed anything meaningful but respect to Maskaev. Good wins, and legendary KO's.
I like both fights, Oleg KTFO'd Rahman through the ropes the 1st time. And was going to do exactly the same in the 2nd fight when Jay Nady saved Rahman from flying through the ropes again. Though I'm sceptical about Oleg's chances in h2h historical fights because of his speed and chin limitations, I like him and he's an example of overachiever who won the title years after literally everyone wrote him off.
Interesting, as there was a " This content is protected " which prevented many talented Eastern European block boxers from going professional. Oleg Maskaev was something of a pioneer, a Russian turning professional in 1993. On film, Oleg Maskev shows better form and power, but Harry Wills obviously is the more significant of the two. Wills who wasn't very fast and only moderately skilled ( On the three films I have seen ) would be the smaller man in this fight. In his prime, Wills almost always enjoyed a size and age advantage over his best opponents. I'd pick Wills via later round TKO, but realistically this could go either way.