I think this is a pick 'em fight....

The fight plan for Bowe
Use the height, use the jab, tie up on the inside. Use your superior athletic ability to move and counter.

The fight plan for Tyson
Slip the jab, cut off the ring, use angles to attack and counter. Apply steady pressure, throw punches in combinations, and to cheat a little initiate the clinch, break early and fire off combinations.

Why Bowe wouldn't win
As dominant as Bowe was, he NEVER fought a big time power puncher like Tyson or anywhere near Tyson. Riddick got rocked by Holyfield and at times despite his physical abilities he had the tendency to be lazy in the ring, allowing himself to take punishment and allowing shorter fighters to fight on the inside.

Why Tyson wouldn't win
Mike Tyson had a weak psyche and if he was stood up to he could be broken. Riddick Bowe for whatever flaws he had, he possessed an enormous amount of heart when challeneged. The biggest flaw of Tyson's style was that he had to be in close to do damage and if he was kept at distance and tied up on the inside he could be shut out.

I see it like this.....45% Tyson wins by KO/TKO in the early to middle rounds, 50% Bowe wins by KO/TKO in the late rounds, and 5% Bowe wins by decision.