Trinidad-De La Hoya must be near the front of the queue here. PPV extravaganza, the Puerto Rico versus Mexico rivalry element, both guys in the primes of their life, unbeaten, high knockout percentages. Supposed to be the fight which decided who the Welterweight of the 1990s was and a defining one for the victor. Was even being talked up as another Hearns-Leonard. Instead we got a stinker which did a lot to wash away the prestige of both, with a very disputed and largely unpopular decision at the end on top of all that. A huge let down on what was supposed to be an enormous night for the sport.
Leonard vs Duran in New Orleans. The sad thing about it was though Leonard was winning the fight, he wasn't running away with it. For Duran to quit without at least TRYING to adjust his game plan is one of the most disappointing performances in boxing history, and still hard to believe to this day. I mean it's one of those things before it happened I would've bet my life that would NEVER happen in a fight involving Duran. Then it happened,,,,,, Duran quit.
Most of the disappointments are fights that didn’t happen but May-Pac was disappointing even before it happened, being 5 years past its sell-by date. Another one that was personally disappointing was Jones-Toney and that was due to Toney not taking the biggest fight of his career at that point seriously enough. Jones would likely have always won but for Toney to eat himself out of shape was a terrible letdown.
There was no reason for Trinidad/De La Hoya to not be what Trinidad/Vargas turned out to be: an all-out, classic war.
I actually consider Leonard/Duran III to be worse because at least their fight in New Orleans was memorable and pretty exciting until Duran did the "No Mas" (or "no sigo", depending on who you ask). Their third match was boring as all hell and Leonard made it look like Duran didn't even belong in the same ring as him.
Leonard / Duran lll went pretty much the way I expected. Both fighters were well past their primes and best fighting weight.