Ali in his prime would have (in the ninties) had the most trouble with Bowe, Lewis was fairly static and easy to hit, Holyfield needed a brwaler to look good, Mike wasnt iron any more but would have given Ali a rough ride.

Bowe had good skills ut wasted it, ultimately I dont think there was a nineties fighter that Ali couldnt beat, the older version would have had trouble with any hard workers but the younger one would have had an easier time