Best 90s Heavyweight Fight That Didn't Happen But Should Have?

I agree with Ironchamp on Bowe/Lewis

In 95 - Lewis would take it
Lewis was now with Manny Steward, he had tightened up his jab and defense, and essentially had turned into a complete fighter by 95. Lewis in 95 was a great heavyweight, instead of the raw but nonetheless good/formidable Lewis pre 95.
Bowe was still pretty strong in 95 (see Gonzales fight) and he would have been competitive, but I'd take Lewis because he's the more complete fighter at this point.

In 93 - Bowe takes it
Bowe was significantly more advanced than Lewis in 93. Bowe was prime, Lewis was not. Lewis was still fairly raw in 93, he liked to bomb with his right hand, and he was a big talented guy but he had not harnessed his skills yet. He pawed way too much with his jab, his defense was not as tight, and he just was a sloppier fighter than Bowe at this point.

Bowe in 92-93 was a pretty complete fighter, a guy who would give most ATG heavies a real challenge. He was a fabulous in fighter for a guy his size, he had a great left jab when he used it, he threw a really good crisp right hand, could go 12 hard rounds, had an excellent chin, and had some real heart. His only weakness was that he could no doubt be hit fairly easily, but again he could take a punch, and that was partly a product of the fact he fought such an aggressive style. A 93 Bowe would actually occassionally slip a punch or block a punch, he bobbed and weaved now and again, where as by 95 I'd say that Bowe's defensive skills (while never that strong), had deteriorated. So I am pretty confident that Bowe would have won in 93.

Damn these fights should have happened. I think we would have gotten a trilogy from these 2 had the first fight happened in 93. They would have been the best, most skilled, big man's fight in HW history. The public would have wanted to see them fight again after a great fight in 93.

I think Bowe would have won the 1st fight in 93 by 9th round KO.
Lewis would have won the rematch in 95 by a competitive but clear UD.
And then in 96, Lewis would have knocked Bowe out in the rubber match pretty easily by the 6th round (Bowe too far deterioted here).

So Lewis would have won the trilogy 2-1, but what a great trilogy it would have been. It would have elevated both guy's stock.

I think both a Holyfield Tyson fight somewhere from 89-91, and a Bowe/Lewis trilogy from 93-96 would have elevated the 90s heavies right there with the 70s heavies for all time eras. (in addition to having the Bowe/Holyfield trilogy the same as before).