At the time they could have fought, De La Hoya wins this. Especially since Oscar was always a true Welterweight who benefitted from early weigh ins, and, would have a substantial size advantage over Randall.
When Randall beat Chavez Oscar was still at 135 and only a pro for a little over a year. Randall would have beaten him then. At theiir respective bests at 140 its a very competitive matchup and its not beyond the realm of possibility Randall wins. Oscars resume at 140 consists of a UD over Miguel Angel Gonzales whose peak was at 135 lbs. and a stoppage of a more degraded version of Chavez than warred with Randall two years earlier. After controversially getting the WBC title back from Randall Chavez himself was carefully guided to a $$$ fight with Oscar in 1996 when it wad deemed Oscar was ready to go after a 140 lb title. Lets face it those two were latin market cash cows unlike Randall. The 1996 Oscar would probably beat the 1996 Randall who regained the WBA title from Juan Coggi. However the peak 1994 form of Randall was very high so in a hypothetical peak for peak 140 lb matchup it is not a forgone conclusion that Dela hoya wins
Would have loved to see Randall beat Carr and fight DLH after, buttttt ..... I think it would have been a great fight at 140, but at 147 Oscar is too good and too strong for the surgeon.