OK well this is a tough one to call as Wlad hasn't necessarily fought anyone like Tyson and Prime Tyson never fought anyone like Wlad but just for shits and giggles I'll answer this (objectively, I'll certainly try)
I see the fight a down the middle 50/50...early round stoppages 80/20 in favor of Tyson, later round stoppages and/or a decision 80/20 in favor of Wladimir.
The case for Mike Tyson:
I'm sure if you ask any boxing fan "Which one fighter of all time would really be a threat to Wlad Prime for Prime" plenty of people would say Tyson (lots would say Ali or Lewis, but I think more would say Tyson). Tyson had solid defense, a hell of a chin, and very quick, powerful, accurate hands. Tyson had great balance, he countered very well, and he was able to throw punches in combinations (something to my knowledge Wlad hasn't seen). Wlad is a head hunter and often forgets all about body work and in doing that the crouch and peek-a-boo defense CAN become even more effective as can the rolling and countering. If Tyson could slip the 1-2 and get to the inside to rip off a combination before Wlad tied up then I would safely assume Wlad would either be in big trouble or go down, but either way the fight would be over shortly if that process was repeated. Mike Tyson would need to create angles, make Wlad miss with the right hand, perhaps initiate a clinch, break, and then leap right back in with a combination catching Wlad off guard. Tyson would want to fight a little rougher than Wlad is used to in order to get him off his game (kind of like Chambers tried to) if he's able to distract Wladimir it may be easier to land a big overhand right or left hook.
The case for Wladimir Klitschko:
If anyone has the style blueprint to abuse Mike Tyson's crouched fighting style it's Wladimir. Wlad fights tall, he has a very efficient offense, one of the best jabs in the history of the fight game, and he moves fairly well in the ring. In order to nullify Mike Tyson's attack one needs to know control the space in the ring and Wladimir has learned how to do that very well. Wlad wants to be at distance or tied up and there's no inbetween until the fight is almost sealed up. To make space his friend Wlad would need to pop the jab occasionally hook off the jab (hooking vs Tyson is VERY dangerous) and make sure that right cross is accurate, timed perfectly, and powerful. If Tyson slips his way inside Wlad would need to tie up immediately to avoid Tyson's work to the body and ANYTHING coming up top. The key to Wlad's safety if he misses the jab is keeping the jab out stretched and circling away from danger with (and this is very important) his guard up and tight. If Wlad accomplishes 5 rounds of distance control, ring generalship, and accurate punches it would only be a matter of time before Tyson gave up on himself...he'd slowly stop moving his head, he'd slowly stop trying to find angles or work inside, he'd allow Wlad to tie him up on the inside and he's eat big punches for it.
The height, weight, and reach all favor Wladimir. The handspeed, chin, and combination punching all favor Tyson. I think power is a push, both these guys do damage in the ring and have outstanding KO percentages. Tyson does his work early, Wlad does his late, but both get the result.
I hope I made an acceptable go of it, I did try to be objective, and I hope you don't see my seeing it 50/50 as a cop out, I genuinely see it that way just given the styles and skill levels of both fighters.
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