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- For the last eight months or so of his career, Ric Flair wrestled under a stipulation that should he lose a single match, he would be forced to retire — thus turning all of his matches into Loser Leaves Town matches. He finally lost at Wrestlemania and did indeed retire, making this the rare example of the wrestler actually quitting wrestling when he lost: Flair's real life intent to retire was what sparked the storyline in the first place. It was WWE's way of giving him a big sendoff.
- Then, after that amazing sendoff at Wrestlemania, he wrestles in a tour of Australia alongside Hulk Hogan, and started performing for TNA. It became just another 10-Minute Retirement.
- It is also worth noting that after losing a Loser Leaves Town match to Mr. Perfect in 1993, Flair did not return to WWE until 2001 - and then only because he had (kayfabe) bought a 50% share in the company.
- Matt Hardy and Edge's feud following the controversy surrounding Lita ended with one of these, Matt Hardy on the losing end.
- The Undertaker lost one to Edge at One Night Stand 2008. This removal was for the purposes of recovering from injuries. He returned less than three months later when Vickie Guerrero needed him to kick Edge's butt.
- A stranger example occurred in 1999, where Vince McMahon was banished from the then-WWF for several months as a result of The Undertaker losing a match to "Stone Cold" Steve Austin. What makes this strange is that the time period was essentially the exact time surrounding the WWF's IPO, making many suspect that Vince took himself out of the limelight to comply with SEC regulations.
- William Regal also lost this kind of match. Regal failed a drug test and WWE needed a kayfabe explanation for his suspension that followed said test.
- The reason for the match as opposed to simply taking him off TV was that Regal was in the middle of a major push at the time.
- In the UWF (the former Mid-South territory), "Hacksaw" Jim Duggan lost a "title vs. career" match to the One Man Gang, as a kayfabe explanation of his departure to go to the WWF.
- Kevin Nash & Goldberg both lost Loser Leaves WCW matches to Scott Steiner in 2001, which actually stuck due to the company going out of business before they could be brought back.
- This was actually part of Eric Bischoff's big plan to reboot the company following his plans to purchase WCW. The original idea was to have Steiner wipe out every good guy on the roster on his way to having complete dominance over the company. At around the point where this scenario had played out, the ownership transfer to Bischoff's consortium would be complete. In the inaugural Nitro of his regime, he would bring back all the Faces at once and kick the new company off with a fresh start. Unfortunately, after WCW programming was taken off television in the wake of the AOL/Time Warner merger, the buyout was canceled and WCW itself was shut down shortly thereafter.
- One particularly egregious example from WCW featured Curt Hennig losing to Buff Bagwell in a Retirement Match, only to return to the ring THE NEXT DAY. Needless to say, this was booked by Vince Russo.
- Shawn Michaels was so desperate to end The Undertaker's Wrestlemania win streak, he agreed to put his career on the line at Wrestlemania XXVI. Unfortunately for him, he failed to end 'Taker's streak. Michaels has made a point to make the stipulation stick, though he still appears for WWE from time to time.
- Triple H challenged Goldberg to a one-sided variant of these during the latter's WWE stint, putting the World Heavyweight Championship on the line against Goldberg's career (specifically stating that it was Goldberg's career on the line and not his position on the Raw roster).
- This angle becomes Serious Business in Mexico's wrestling circuit, where if a wrestler loses one such match, the result is actually enforced. Much like losing one's mask, a wrestler better think twice about getting involved in this type of match in Mexico, because should they lose, they won't get a chance to go all "Hahaha, just kidding, here I am back for more action!". They'll be kicked out of that town for real, never to return.
- At Wrestlemania VII the long-running feud between the Ultimate Warrior and Randy "Macho Man" Savage culminated in a "Retirement Match" where the loser had to retire from the WWF (now WWE). Savage lost and retired from wrestling for an entire year, instead working as a commentator. He was eventually reinstated so that he could wrestle against Jake "The Snake" Roberts, who had been trash-talking Savage on the air, and attacked Savage and his wifenote Miss Elizabeth during their "wedding reception" at SummerSlam 91 with a snake.
- This is how Jeff Hardy's final WWE run ended, losing a cage match to CM Punk.
- Chris Jericho has lost two of these in WWE. First to John Cena and a second one to Dolph Ziggler. Neither stuck, although the former lasted for years before his eventual return.
- Subverted at Money in the Bank 2011. Punk was leaving either way, but if Cena lost, Vince would fire him. Despite Cena losing and Punk running off with the title after foiling a cash-in attempt by Del Rio, Vince didn't get to fire Cena due to being fired himself the next night.
- Bruiser Brody defeated Butch Reed and Slick in one of these in the old Central States territory in Kansas City as a formality since they were on their way to WWE.
- Tommy Dreamer FINALLY scored an officially recognizednote pinfall on Raven after two years of trying in a Loser Leaves ECW match at ECW Wrestlepalooza 97, June 6, 1997. Raven was on his way to WCW anyway.
- Mercedes Martinez beat Pune Tang in a loser gets deported match. Two years later, Sumie Sakai would make her debut on the same program.
- While not a "retirement match", Nikita Fink really did stop wrestling after being defeated by Alexis Laree in a loser leaves OVW match.
- Jimmy Jacobs and Jack Evans sent London and Kendrick out of Dragon Gate with a victory in one of these types of matches. Jacobs also sent Sal, The Man Of A Thousand Gimmicks, out of Juggalo Championship Wrestling after a best of three series.
- Given pink slips count, TNA's infamous "Feast Or Fired" matches can result in the winner leaving town. Most famous victim being Christopher Daniels.
- Vince Russo era WCW had a "Pink Slip on a Pole March", where confusingly the one who got the pink slip didn't get fired.
- After spending two years Brainwashed and Crazy due to the effects of the Eye Of Tyr, Delirious vowed to torment UltraMantis Black for two years as equal payback once freed from its influence. This lead to a loser leaves Chikara match, which UltraMantis won.
- In the Discworld a witch that loses a duel will generally leave town. Being publicly defeated makes it hard to maintain authority, and most witches are proud enough not to want to stick around people who've seen them lose.
- Robbie Rotten frequently employs this trope on LazyTown as a way to try to make Sportacus leave the titular town.note It's so predictable that Sportacus lampshades it in an one of the earlier episodes.
Robbie: If I win, you have to leave Lazy Town forever.Sportacus: The usual, right?
- DefJam: Fight For NY has Crow challenge D-Mob to one of these, with the stipulation "Loser goes to Jersey".
- Mac's Last Stand in Punch-Out!! (Wii). Except that Mac needs to lose three matches to end his career. (This was actually the standard in Punch-Out for the NES.)
- In the Rifftrax version of The Bourne Identity, Mike claims that "Sniping someone is no way to settle your differences. Give me an old-fashioned 'loser leaves town' wrestling match any day." Kevin then realizes that this is the true story behind Mike's move to San Diego. Mike also claims Tom Brady happened to be in the south of France after losing such a match.
- One episode of Goof Troop had wrestling champion "The Incredible Bulk Brogan" declare one of these. It turned out the reason why is that he didn't want to wrestle anymore and needed a way to bow out.
- My Little Pony: Friendship is Magic:
- Trixie's demand to Twilight Sparkle in "Magic Duel". And Twilight actually gets kicked out! In the best spirit of the show Twilight uses lies, trickery and deceit to return and beat Trixie in a rematch.
- Played with in Pinkie Pride. The initial deal is that the winner of Pinkie Pie's and Cheese Sandwich's contest would get to plan Rainbow Dash's party, and the loser... DOESN'T. In the end, after Pinkie loses, she ends up leaving town anyway... until stopped by the other characters.
- Sonic Boom: "Blue With Envy" has Sonic challenging the Totally Radical Swifty the Shrew to a foot race around the village, with banishment as punishment for the loser. Sonic thinks his superior speed won him the race, but he soon finds out that Swifty had already beaten him to the finish line. Or rather, a Swifty crossed the line first, as Eggman reveals he'd built an army of Swifty the Shrews just to mess with Sonic.
- Sports championship tournaments can end up this way (if "town" is defined as "still alive for the championship") depending on how the system is set up; likely the organizers set it up that way to invoke this trope for the drama, among other reasons. For example, a given NFL team is scehduled face a team no more than once in the regular season (except against the other three teams in its division, which a team will play twice). If a team were to play another team a second time (third in the case of a division rival), it will be in the playoffs where the stakes are almost certainly higher (i.e., the loser's done for the year). The trope is not limited to the playoffs themselves, either. In recent years the NFL has scheduled all Week 17 (the final week of the regular season) games between division rivalsnote - this combined with flex-scheduling (which allows TV networks to pick the most interesting games to broadcast nationally in prime-time just one or two weeks before) and some luck has meant that Week 17 Sunday Night Football matchups the past few years have all been games where the winner earns the division title (and automatic playoff spot) and the loser goes home for the season, a huge boon for TV ratings.
- This trope becomes more appropriate in sports leagues around the world that have a system of promotion and relegation, in which the worst-performing team(s) are sent to a lower-tiered league in exchange for the best-performing team(s) in the league below. Thus, some late-season matchups between two relegation-threatened teams might have a Loser Leaves Town feel to them. This system is standard in European football leagues and most other team sports in Europe. Uniquely among individual sports, sumo wrestling in Japan uses promotion and relegation, with the exception that any sumo wrestler who achieves the highest rank of Yokozuna can never be relegated out of the top level no matter what. Instead, a Yokozuna is supposed to as a matter of honor retire when he can no longer compete at the highest level.