This may not be as cut and dried as people think. They were similar in size, both short and muscular. Tyson was quicker and a harder puncher. Oscar was strong as hell with an awkward style that caused a lot of problems for fighters. Oscar was absolutely fearless and wouldn't walk into the ring against Tyson cowed and scared the way most of Tyson's opponents were. Bonavena went toe to toe for 25 total rounds against Joe Frazier and was never even seriously hurt, let alone dropped. He was stopped only once in his long career. That came against Ali in the 15th round, fatigue probably being the main factor for the stoppage. As he showed against Holyfield, Tyson could be cut down to size by a strong fighter who stood up to his bullying tactics. Anybody give Bonavena a chance in this matchup? Personally, I think Oscar would have a fair chance at pulling off an upset.
I agree that Oscar would have given Tyson a good tussle, as like you said he was absolutely fearless in that ring and was also an exceptionally strong fighter physically, and I can see him pushing Mike around quite a bit in close quarters as Mike was never really effective when in close quarters combat and was easily tied up by his opponents, and Oscar sure as heck was strong enough to tie up Mike on the inside. He also had a damn good chin, which was definately in evidence in the second Frazier fight which I have in its entirety, as he took some absolute bombs from Joe in that one yet stood his ground with him every step of the way. But when all is said and done Mike was the superior fighter, as he had the better defense and punching power, as well as being the better combination puncher of the two. Oscar would make a fight of it though and would make Tyson work hard for the win, and I certainly think he was tough and durable enough to last the distance with him. However, for the reasons I outlined above I think he would lose a competitive but somewhat one-sided bout on the cards. It would have been a good one though, and I would have loved to see these two jawing at each other, especially with their high-pitched voices, now that would have been comedy at its finest!
Oscar loses this one on the cards, but gives Tyson one of the longest nights of his life. UNLESS, Tyson got frutrated and fell apart when it got to round 13 or 14 and Oscar is still pushing him around and taking his best shots. In that case Oscar wins by KO. Boo
Just because Bonavena is great because he lost to Frazier and Ali doesn't mean he'd beat Tyson. He'd probably lose in a Tucker-like effort.
Bonavena was tough, no doubt. But against prime Tyson he would be giving away 15lbs, which would be a factor and Bonavena's face first attack would not be an ideal attack to face a 87/88 Tyson. Bonvena had an excellent chin and would give Tyson things to think about, but Bonvena would not have the one punch power to worry Tyson. So I take Mike to win on a late stoppage, but not without picking up a few bumps and bruises on the way. Tyson TKO10
Bonavena was a very tough durable guy, with a tremendous chin. He may not have been the heaviest punchers, but wasn't without his fair share of boxing skill. I think Bonavena might take a peak Tyson the distance and would put up a fearless, heroic (despite enevitibly falling short). He'd drop a fairly wide UD but would have his moments. Over the course of a 15-rounder: something like 10-5, Tyson.
I think Tysons speed would be a problem for Oscar but Oscar could get in close and bully his way in with his strength but Oscar had clubbing power, a lil better than decent, he threw awkward roundhouse shots that could catch you, but I like Tyson by a stop
It would be like a Super Middleweight fighting a Light Heavy. Sure it would perhaps not be a deciding factor in a potential victory, but it would need to be addressed when putting accross a hypothesis of the fight.