Re: Jerry Quarry vs. Vitali Klitschko
It depends: if Vitali boxes on the outside and doesn't get dragged into a brawl, he could embarass Quarry (who didn't like to have to look for his opponent). On the other hand, Vitali usually went forward in a linear, plodding and predictable manner, with a very limited range of punches. He's very open to being counted.
Of course, there is the question of height, but Vitali was very good at giving up his height advantage. If Quarry uses a bit of head-movement to avoid counter-right hands (something Vitali wouldn't have really seen before), I think he would find it pretty easy to use Vitali's wide-stance/low hands means of eliminating his height advantage.
Quarry's bodypunching was very good, and I don't think Vitali had the handspeed to counter before Quarry has gotten too close. Once Quarry's in close, Vitali's vast height disadvantage would allow Quarry to dominate him in close.
If they both fight as they have in their best fights, therefore, I think Quarry would win a firm UD.