It's easy to mock the dude for fishnets and skinny jeans, but gotta give Oscar his due. He was truly tough and his resume, win or lose, was filled with killers. Outside the two very late career stoppages, he was very much in every fight he lost on the cards; Floyd, Mosely x2, Felix. Despite all the Hollywood phoniness, he came for battle. It's just that this is a battle he would lose.
It would be a good competitive fight for a few rounds, then I think Duran would take over and break Oscar down. Duran’s body punching and better stamina make it really rough for Oscar in the late rounds. Oscar was tough so I’ll say he guts his way to the final bell in dropping a 8-4, 9-3 type decision
Montreal Duran surely wins, but De La Hoya has a punchers chance if he times Duran with the left as he comes in, but Duran probably doesn’t give him any room, mauls him, and potentially stops him.
Duran at welterweight was just as formidable as he was at lightweight. In fact , arguably , he beat two of his best opponents at that weight in Ray Leonard and Carlos Palomino while they both were prime or close to it. Hoya is not to be underestimated, and would trouble almost any welterweight in history at his best. But Duran would eventually take him into the deep water and drown him. Duran stops Hoya with in 12 rds.
But the physical mismatch is still there though. Duran has to still get under Tommy's jab and survive a right or two.
Oscar is no slouch, he will touch up Duran . He may even put him down, but Duran imposes his will and breaks Oscar down in 10. Oscar is faster in a straight line than Leonard and is bigger and can manhandle him a bit - but he does not have the footwork and combinations that Sugar Ray had. He most certainly does not have the stamina to stay in it all 15. Oscar would have to have that killer instinct that Ray Leonard had , but lets face it , Hoya just ain't that guy. Duran will break him down and stop Oscar. Oscar is a bit of a front runner and just cant dig deep enough.