Triple H's feud with Cactus Jack ends with him retiring Mick Foley at No way Out 2000. Mick Foley kinda gets a Hope Spot by being reinstated for one night to compete in the title match main event at Wrestlemania 16 (or 2000 as it was also title in honor of the new millennium) but he just ends up getting eliminated in the middle of the match by Triple H
Speaking of which up to this point all Wrestlemania's ended with the baby face winning at the main event. However Wrestlemania 16 ended with Triple H beating The Rock thanks to Vince McMahon turning on The Rock. Even though The Rock kinda got revenge by rock bottoming and people's elbowing Stephanie McMahon at the end, Rock still lost the match. At least The Rock overall won the feud.
Wrestlemania 17 ended with Stone Cold turning heel and teaming up with Vince McMahon.note Though since it was in Steve Austin's hometown of Texas, the crowd loved it and treated it like a Vince McMahon face turn instead.
Triple H's feud with Booker T in which he went on about how people like Booker T don't get to become champion and after all the build up to Wrestlemania 19 with this story line-Triple H wins. This was hugely criticized by fans for a varied of reasons ranging from how Triple H came off as a huge racist in the feud and by beating Booker T essentially proved the racist was right, to how it took at least a minute for Triple H to pin Booker T after hitting the pedigree on him which in turn made Booker look really weak.note Worse, that wasn't even the plan. Triple H botched the move, hence causing the delay, but just went ahead with the follow-up pin despite that.
Undertaker's legendary winning streak at Wrestlemania tragically coming to a end when Brock Lesnar beat him at WrestleMania 30.
Survivor Series 1997, depending on whose side you are on could count for this. The Montreal Screwjob where Bret Hart legitimately got double crossed and screwed out of his belt and also humiliated in his home country.
At Ultima Lucha in season 1 of Lucha Underground, pretty much every heel won their match with maybe only on or two exceptions.
A year later at Ultima Lucha 2, Pentagon JR had a big rematch against Matanza for the title where he trained intensely to beat him, yet Matanza still wound up winning against Pentagon JR.
Dusty Rhodes never got any revenge against Ted DiBiase who pretty much beat Dusty in every match they had.