Holmes is the more proven commodity here. Bowe looked like an emerging superstar in 1992. A guy that would dominate for years to come. Holmes was more steady if unspectacular but he stood the test of time and was way more consistent than Bowe was. His career had longevity and focus. It is possible that Bowe could break through ala Snipes but Holmes had great recuperative powers and was as tough and determined as they come. Holmes by UD or even possibly late stoppage.
Bowe is not that big of a single shot puncher and needs to string together combos to get the job done. The problem is Larry is not going to stand in front of him and allow him to fight that kind of fight. Bowe couldn't catch a novice fighter in Donald and the legs and jab and tools of a Larry Holmes are on a different stratosphere than Donald. Actually, I don't even see Bowe winning many rounds and just getting turned all night and peppered. Trying and hanging in there and that's about it. And he definately is not landing an uppercut on Holmes--he was very difficult to hit with that punch. so subtract Riddick's best punch. Eventually those jabs will swell up those Bowe eyes and either the swelling or a cut would likely see Holmes with the late tko victory.
I'd favour Holmes. But Bowe would give Holmes hell. Snipes had a 1981 Holmes down and on ***** street, I think Bowe's got a great chance of causing Holmes some very serious difficulty.