How was the 2000 version of Oscar any better than he was against Mayweather? He only had better speed, he had no right hand, he didn't have as good of defensive skills, and he over threw his jab which a fast guy would eventually counter over and over again. Also when he would get tired late like he always does and did, he was naturally smaller back then and easier to hurt than later on.
Mosley would be a better fight, but he still doesn't have the boxing skills to beat Mayweather, he had already started to look different from the dominant, brilliant lightweight he was, the combinations weren't as natural or thrown as often, his jab has never been that good, and he would load up on punches Floyd would see coming from a mile away. It would be close just because MOsley is so strong and so fast, but Floyd would win a close fight against Shane if those two versions of them fought. Shane is a much bigger guy with the same speed and much more strength, but he doesn't have the boxing skills.
Robinson was just so physically dominant, and he was adept at fighting on the outside, I doubt he would catch Floyd cleanly very often, but he would have won because he would have kept Floyd on the defensive all night much more effectively than Oscar.
Leonard: I think its a toss up, but Leonard's size advantage and adept ability to fight on the outside would have made it very tough for Floyd. Their similar speed would offset that advantage for either guy, but I think Leonard is the more offensive guy so more often than not the more active guy gets the nod. I bet Floyd would land more punches if they fought though.
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