No. Ruddock still wasn't at his best and as people have alluded he'd trade punches with Tyson which isn't the way to go. He'd likely last longer than Bruno, though and fare well until being stopped later in the fight.
It probably would've gone pretty similar to the '91 fights. I don't think '89 Tyson was significantly better, not to the level that would make enough difference. Both guys would come away with sore heads and mutual respect. I guess the biggest thing is that Ruddock wouldn't have been seen as the 'heir apparent' since Mike would still be around and not in jail...he'd have had to get back into the mix. Maybe we'd have had Ruddock vs Holyfield in 1990 or something...
I think Tyson actually looked a bit sharper and in better shape during his '91 fights than he did in the first fight against Bruno. I just don't think the Ruddock of '89 was quite as good as the '91 version: hence why the Tyson of '89 would stop him late, I think.
Hard to bet against Tyson at that time, but everyone knows what happened in Tokyo. Ruddock vs Tyson was originally scheduled in Edmonton but Tyson apparently pulled out due to breathing and chest complications. I think Razor would have given Tyson a very tough fight with a decision going either way. The potential was there for both men to knock each other out, but I think Ruddock vs Tyson circa 1989 would have gone the full 12 round distance. Ruddock was stopped prematurely by Richard Steele in his first fight against Tyson and foolishly tried to knock him out one punch style, with his left-hook-uppercut smash. Ruddock disappointed many fans and trainers throughout his career by neglecting the jab that gave him his nickname in a lot of his fights, especially against Tyson and Lennox Lewis. It was a razor sharp punch, that I've heard was comparable to that of Larry Holmes and Sonny Liston.
Ironically, it was a jab against Lewis that got him into trouble... But yeah, he was more of a stick 'n' mover when he began his career. Like so many boxers, he was a big fan of Ali and wanted to copy that style. It seemed to be after that Jaco loss and the split decision against Weaver that he changed things up.