Listen we saw a fit and focused Tyson in the Ruddock bouts. By then the head movement had wained and he still came straight on looking for single shots. Douglas would have boxed him around the ring again IMO.
If Douglas was 1:42 at the bookmakers, in the rematch I would give him a 1:45 chance, or 1:50. The biggest (or one of the biggest) surprises in professional boxing doesn’t happen twice in a row.
There wee two times when this fight was realistically on the cards. One was obviously Douglas's first title defense. The fight was also mooted during Douglas's comeback, until of course he lost. I don't really see Douglas pulling the trick twice in either scenario. He was obviously not in anything like the condition of the Tyson fight, when he defended against Holyfield, and by the time of his comeback he had slipped more than Tyson.
Scenario 1 Mike Tyson reunites with Kevin Rooney addresses his weaknesses and forms a strategy to beat Buster Douglas and come back more disciplined, drilled motivated and in all probability stops Douglas in later rounds as Douglas gets frustrated with Tyson's head movement and slipping and gets lackadaisical and likely gets dropped or stopped. Scenario 2 Douglas takes immediate rematch with Tyson comes in conditioned , fit and focused, despite Tyson training hard for the rematch he still loses due to the preponderance of sycophants and yes men. Scenario 3 Douglas allows the legal action held against him to affect him mentally consumes too much food comes in overweight and undertrained. Rematch version of Tyson beats him with very little resistance. Scenario 4 Douglas comes in shape against Holyfield goes into battle and scrapes a split or unanimous decision. The fight takes a lot of Douglas and comes in depleted against and a motivated Tyson and in all probability loses a unanimous decision due to bias towards Tyson and him outworking Douglas despite coming back with the same team in Tokyo. Scenario 5 Douglas manages to take two or three easy title defences stays in shape and meanwhile Tyson takes on hard fights ala Ruddock twice, they then have a rematch, Douglas still fresh and fit beats Tyson easily in rematch.
That fateful night in Tokyo the stars were aligned and we had a peak Dougals versus a subpar Tyson. That situation was not going to happen again. Hence assuming in any rematch scenario we have a peak or almost peak Tyson, then It all comes to what version of Douglas shows up. If Tokyo Douglas shows up, then it is 50%-50% chance split with Tyson If Free Willy Douglas shows up, then it is 100% sure Tyson wins and probably in 3 rounds or less.