The Retirement Match, or some variation of it, might be the longest running gimmick match in wrestling history, next to the battle royal and steel cage. In the older days of regional promotions, these matches were billed as "Loser Leaves Town" matches, where the loser would simply move to another wrestling company down the road. Another popular variation that sprung up was the Career vs Title match, where a wrestler put his entire career on the line to get a shot at the championship. As the Monday Night Wars heated up, they became an easy way to write off guys jumping between WCW and WWE. And finally, in the more recent brand extension, they were prevalent when guys went from RAW to SmackDown and back again.
However, despite the built-in high stakes, these matches can be hugely disappointing. Especially in the era of dirt sheets and internet news, the winner can be obvious weeks in advance. Even if it's any kind of swerve ending, most of the time the retirements only last long enough for a wrestler to rehab an injury or film a movie. The below matches are the most disappointing examples, featuring several matches both old and new across the WWE and WCW. After watching through these matches, any wrestling fan is going to want to permanently retire the retirement match.
15 15. The Rock vs Mankind - Pink Slip on a Pole Match, RAW 1999
The Rock and Mankind had some great matches, but this would not be one of them. It was almost doomed from the start for being backwards - you retrieve the pink slip off the pole and then the other person needs to leave for good? Backing up again, there hasn't really ever been a good "thing on a pole" match in history either. The Rock would win this one despite some interference from Al Snow. But like most of Mick Foley's retirements, this wouldn't stick, and he would be reinstated after the roster threatened a walkout just two weeks later. The best thing to be said about this match is that it led to the return of Cactus Jack and a classic retirement match inside Hell in a Cell.
14 14. Matt Hardy vs. Edge - Loser Leaves RAW/MITB Ladder Match, RAW Homecoming
On paper, the Matt Hardy vs Edge feud over Lita was a no-brainer. Edge was one of the hottest rising stars in the WWE, the real-life drama was red hot, and the two had been famous foes at the height of WWE's popularity in TLC matches. Their previous matches at SummerSlam, Unforgiven, and a RAW street fight had all been pretty solid.
However, this ladder match didn't live up to the others. Edge with the briefcase was red-hot, with no chance of losing it. The ending to the match was just pure torture for Matt - with Lita holding him in the ropes as Edge won and took in all the glory. It felt weirdly sadistic - at least emotionally - to watch the villain win so definitively. After only two months, it felt like a really abrupt blowout match. It also buried Matt Hardy to SmackDown, while Edge would become WWE Champion shortly after.
13 13. Chris Benoit vs. Kevin Sullivan, Bash at the Beach 1997
This was a great feud, lasting over a year, with several good matches along the way. It was also a pretty solid match and blow-off to a big storyline. Even better, the right person won, with Sullivan putting over the young Benoit. Even better, Sullivan actually disappeared from TV after his loss. So why is it here?
Much like the previous entry, the out of the ring ramifications dwarfed the actual match. Sullivan had been a wrestler-booker in WCW, and this loss allowed him to focus more on being the latter. He didn't have much sway under Vince Russo, but still developed professional rivalries with some of the best talent in WCW. The Radicalz (Benoit, Guerrero, Saturn, and Malenko) left WCW in 2000 abruptly due to Sullivan's ascension to the top booker spot. This was one of the first huge hits that led to WCW's demise in 2001 and it all led back to this retirement match.
12 12. Ric Flair vs. Mr. Kennedy, No Way Out 2008
In late 2007, Ric Flair started on a series of matches where Vince McMahon ordered that if Flair lost, he would be retired. It was a great story that culminated in Shawn Michaels' unforgettable Wrestle?ania moment, saying "I'm sorry, I love you" before Superkicking Flair into oblivion. However, most of the matches leading up to this weren't as memorable.
The Kennedy match wasn't particularly awful, but with WrestleMania looming and an obvious HBK match, there was zero drama. Kennedy was a rising star, but he wasn't going to retire Ric Flair, and he sure wasn't going to do it at No Way Out with WrestleMania just next month. The same applied to his previous matches with MVP, Umaga, Steven Regal, and others. This just gets the notoriety as being the last placeholder before the "real" match.
11 11. Layla vs. Michelle McCool - Loser Leaves WWE, Extreme Rules 2011
The great team of LayCool had been one of the best parts of the Divas division during its run. They were four-time champions and McCool was even Pro Wrestling Illustrated's Woman of The Year in 2010. However, the breakup, feud and blow off match seemed rushed by McCool's abrupt decision to retire. Even worse, the match tacked on another Diva's debut to the end, not allowing the angle to stand on its own. The best thing to say about it, is that it's the rare retirement match that actually resulted in a retirement.
10 10. Kevin Sullivan vs. Cactus Jack - Loser Leaves WCW, Fall Brawl 1994
This match was another prime example of squandered potential. Just months after winning the WCW tag titles together, Sullivan and Cactus Jack broke up and started feuding. They were both on their way to being hardcore icons, but their match left much to be desired. It was a 6-minute footnote where the winner wasn't ever in question. Prior to the match, Cactus Jack was already being promoted as part of a WCW/ECW crossover and wrestling matches for Paul Heyman's renegade outfit. Not surprisingly, Foley went on to better things in ECW and Sullivan continued his stranglehold of power in WCW.
9 9. Ric Flair vs. David Flair - If Ric Flair Lost, He'd Retire, Great American Bash 2000
It's a shame to see Ric Flair on this list twice, because even when he's bad, he's usually good. But even Ric couldn't save a match with his awful son, David, firmly lodged in WCW's Russo-esque death throes. Ric Flair may have more retirement matches than the rest of the wrestling world combined, but David proved the apple fell from the tree in this match. Of course, he then beat Ric in a retirement re-match. Regardless of that outcome, both Flairs would nonetheless stay on WCW TV constantly until it was put out of its misery in early 2001.
8 8. Chris Jericho vs. John Cena - You're Fired Match, RAW 2005
This contest was actually a fairly good match, and a worthy rematch from a good SummerSlam Main Event between the two the night before. But for lifelong Jerichoholic,s it was brutal to watch the new chosen boy, John Cena, continue his unbeatable streak by seemingly retiring Jericho in his prime. The insult to injury with this match continued when Jericho was carried out, kicking and screaming, by security. He was a heel, but Jericho deserved just a little bit of dignity. His legacy would be revived by a great run upon his 2008 return, but in the moment, this match was a travesty.
7 7. Triple H vs. Goldberg - Title vs. Career, Unforgiven 2003
Normally, someone knocking off Triple H in the year 2003 would be a momentous occasion, but Goldberg's time had way passed and this match had all the passion of a stale fart. One-sided retirement matches are always kind of lame and this one was no exception. It was even compounded by the stipulations lining up AGAINST the heel champion, as the title would've changed hands if Triple H intentionally got disqualified or counted out. The convoluted stipulations didn't even wind up factoring into the match, as Goldberg won a mostly boring match with his Jackhammer finisher.
6 6. Marc Mero vs. Sable - Loser Leaves Town, Over the Edge 1998
The Mero/Sable feud was one of many parts of the Attitude Era that are uncomfortable to look back on. This match was set up as Mero vs Sable's hand picked fighter. With all the intergender violence leading up, it was no surprise when Sable picked herself. The only good thing to be said about this match is that it was short. Mero laid on his back shortly after the bell rung and then rolled up Sable for three when she tried to pin him. At only 20 seconds, it's the shortest match on the list. Sable was becoming the female version of Stone Cold Steve Austin and it surprised no one that she came right back. Marc Mero wouldn't get any more traction in the crowded midcard and both of them would be out of the company within a year's time.
5 5. Scott Steiner vs. Kevin Nash - WCW Title Retirement Match, Superbrawl Revenge 2001
You'd think a WCW World Title PPV Main Event wouldn't need any stipulation, much less THREE, but then, you're not Vince Russo in the WCW's final weeks, so this match was a two out of three falls match, a falls count anywhere match, and a match where the loser had to retire from WCW. This was the next to last WCW PPV in history, and the shotgun approach to booking was never more evident than during this main event. Kevin Nash pinned the champion in 17 seconds (narrowly beating the previous match), but Ric Flair immediately added on the 2/3 falls match stipulation. The second fall came when Flair added the "Falls Count Anywhere" stipulation, so that Steiner couldget a pin outside of the ring. The rest of Steiner's win is just a tidal wave of interference and ref bumps from Midajah and Ric Flair. Kevin Nash would leave WCW after this match, but then again, WCW would cease to exist in about three weeks anyway.
4 4. Hulk Hogan vs. Billy Kidman - Winner Gets A Title Shot/Hogan Would Retire If He Lost, Great American Bash 2000
The idea of a Kidman and Hogan feud is already a little absurd, even before we discuss the hurricane of Vince Russo being involved. But with Russo's insane booking, it was a complete disaster. This was only a couple months after Hogan returned from another absence. So it was at least somewhat possible that Kidman might send him on another sabbatical and get the WCW World Title shot that eluded other earlier Crusierweight stars like Chris Jericho, Rey Mysterio, and Eddie Guerrero. But, instead, Hogan continued his cheating-face ways and hit Kidman with the one two punch of brass knuckles and his very real Creative Control clause. Also, Great American Bash 2000 will go down in history for having two of the worst Retirement Matches ever on the same night.
3 3. Hulk Hogan vs. Kevin Nash - Retirement Match For The WCW Title, Road Wild 1999
It makes sense that two of the worst wrestlers and frequent offenders on this list end up this close to the top when they finally faced off. This was billed as the rematch of the "Fingerpoke of Doom" match, one that should be near the top of any Worst Match Of All Time list. Hulkamania prevailed here, but the match was incredibly slow and typical of the main events in late WCW that had no effort from the biggest stars. Nash would stay retired a month or so, but would, of course, return as part of yet another nWo version in October of the same year.
2 2. Andre The Giant vs. Big John Studd - Andre's Career vs. 15.000 Dollar Bodyslam, WrestleMania I
It's hard to rate the old Andre the Giant matches that were more spectacles than wrestling matches. But this was one of the main events of the first WrestleMania and it was completely dreadful. Andre was undefeated at this point, and he had to body slam Big John Studd and win $15,000 or end his career. This shouldn't have really been hard - Andre was the Giant, of course. This concept made way more sense two years later at WrestleMania III, when Hulk Hogan made history by bodyslamming Andre. Anyway, Andre was a rising star nowhere near retirement, and he was easily able to take care of Big John Studd and continue his monster run.
1 1. Goldberg vs. Brock Lesnar, WrestleMania XX
And then, 19 years later, the WWE reached the platonic ideal of the horrible retirement match. The double retirement match. This wasn't an official stipulation, but the crowd and everyone watching at home knew they were both leaving for other pursuits. So why should they care? The WrestleMania crowd was brutal, booing both wrestlers when they did anything. Special Referee Steve Austin basically had to beg them to hook up and, even then, it wasn't pretty. After sleepwalking through their signature moves, Goldberg mercifully ended the match and disappeared from WWE forever. There were really no winners, although the suffering fans did at least get a couple of Stone Cold Stunners and middle fingers after Austin took out all their collective frustrations on the two.