Wrestling Retirement Matches That Went Terribly Wrong

Wrestling Retirement Matches That Went Terribly Wrong


February 17, 2025 | Alex Summers

Wrestling Retirement Matches That Went Terribly Wrong


Farewells Gone Wrong

Watching your favorite wrestling legends receiving a bad farewell is not a pleasant experience. Unfortunately, there have been incidents in the history of pro wrestling where even the stars have faced embarrassment. Check out the worst retirement matches.

Intro

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Kurt Angle In WrestleMania 35, 2019

Kurt Angle was supposed to face Baron Corbin in his retirement match, so fans assumed there would be some kind of surprise leading up to WrestleMania. However, nothing changed; the audience showed no interest in the action.

Kurt Angle In WrestleMania 35, 2019Kurt Angle competes in his Farewell Match on The Grandest Stage of Them All: WrestleMania 35 by WWE

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Kurt Angle In WrestleMania 35, 2019 (Cont.)

The game itself wasn’t bad, but the match was made relatively simple. It was a sluggish, uninteresting decision and the worst one WWE could have made, considering the criticism fans were directing at Corbin. The match concluded with Corbin defeating Angle.

Kurt Angle In WrestleMania 35, 2019Kurt Angle is ‘grateful’ to retire at WrestleMania 35 | WWE on ESPN by ESPN

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Shawn Michaels In Crown Jewel, 2018

In 2010, Shawn Michaels had the ideal retirement match and then came back for a final fight in 2018, which was absurd. Michaels teamed up with Triple H to take on Undertaker and Kane. While Michaels & Triple H won, many mistakes and injuries made this one of the worst-ever spectacles. 

Shawn Michaels In Crown Jewel, 2018Shawn Michaels coming out of retirement as D-Generation X reunite: Raw, Oct. 8, 2018 by WWE

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Shawn Michaels In Crown Jewel, 2018 (Cont.)

Speaking of injuries, Triple H suffered a legitimate torn pectoral muscle during the bout, which significantly affected the match’s quality. Reflecting on this return, Michaels expressed regret and acknowledged that the performance did not meet the high standards of his previous matches.

Shawn MichaelsDX VS Brothers Of Destruction - Crown Jewel 2018 by Wrestling Trope Alert

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Ric Flair In Ric Flair’s Last Match, 2022

Ric Flair had the most recent match in 2022 at an event centered around his retirement. He was in his seventies and matched alongside his son-in-law to face Andrade El Idolo, Jeff Jarrett, and Jay Lethal. 

Ric Flair In Ric Flair’s Last Match, 2022Select Highlights | Ric Flair’s Last Match | Bret Hart, Mark Calaway (Undertaker) Sitting Ringside by Connecting People Through Wrestling

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Ric Flair In Ric Flair’s Last Match, 2022 (Cont.)

While Flair and Andrade won, the match was fraught with challenges. He later revealed that he passed out twice during the bout due to dehydration and, upon medical evaluation, discovered he had suffered a legitimate heart attack during the match.

Ric FlairSelect Highlights | Ric Flair’s Last Match | Bret Hart, Mark Calaway (Undertaker) Sitting Ringside by Connecting People Through Wrestling

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The Undertaker In WWE Super ShowDown, 2020

Even though The Undertaker had a big cinematic farewell at WrestleMania 36, his last actual match inside a wrestling ring happened at Super ShowDown 2020. He made a surprise appearance in the Tuwaiq Trophy Gauntlet match.

The Undertaker In WWE Super ShowDown, 2020Undertaker’s shocking entrance: WWE Super ShowDown 2020 (WWE Network Exclusive) by WWE

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The Undertaker In WWE Super ShowDown, 2020 (Cont.)

The match was chaotic, as R-Truth unexpectedly took down several big names before AJ Styles emerged victorious. Then, The Undertaker showed up and easily took down Styles in a poorly planned decision. Sadly, this ended up being Taker’s last match, and it wasn’t very memorable.

The Undertaker In WWE Super ShowDown, 2020Undertaker’s shocking entrance: WWE Super ShowDown 2020 (WWE Network Exclusive) by WWE

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Kevin Nash In WCW Road Wild, 1999

At WCW’s Road Wild event on August 14, 1999, Hulk Hogan defended the WCW World Heavyweight Championship against Kevin Nash in a retirement match, with a stipulation that the loser would retire from professional wrestling. 

Kevin Nash In WCW Road Wild, 1999Kevin Nash vs. Hulk Hogan - WCW World Championship Match: Nitro, Jan. 4, 1999 by WWE

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Kevin Nash In WCW Road Wild, 1999 (Cont.)

Hogan secured the victory and forced Nash into retirement. However, Nash’s retirement was short-lived, as he returned to wrestling just a few months later, which made the entire stipulation pointless. The bout was criticized for its lackluster performance.

Kevin Nash In WCW Road Wild, 1999Kevin Nash vs. Hulk Hogan - WCW World Championship Match: Nitro, Jan. 4, 1999 by WWE

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Mankind In RAW, 1999

The Rock faced Mankind in a Pink Slip on a Pole match on RAW on December 27, 1999, where the loser would be fired. The match was part of a rivalry between The Rock and Mankind’s team and Triple H’s group. 

Mankind In RAW, 1999FULL MATCH - The Rock vs. Mankind – WWE Championship Match: Raw, Jan. 4, 1999 by WWE

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Mankind In RAW, 1999 (Cont.)

In a tough match, The Rock won against Mankind, which led to his firing. However, just a few weeks later, he was brought back by WWE, making the whole stipulation pointless. Mankind soon competed in the Royal Rumble.

Mankind In RAW, 1999FULL MATCH - The Rock vs. Mankind – WWE Championship Match: Raw, Jan. 4, 1999 by WWE

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Triple H In RAW, 2021

On January 11, 2021, Triple H wrestled his last match on RAW against Randy Orton. The fight didn’t have a real ending because Alexa Bliss, working with Bray Wyatt, interfered and threw a fireball at Orton. 

Triple H In RAW, 2021Triple H and Randy Orton meet before WWE Super ShowDown: Raw, June 3, 2019 by WWE

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Triple H In RAW, 2021 (Cont.)

Later that year, Triple H suffered serious heart problems and heart failure, which almost cost him his life. This was not an ideal farewell, but due to health issues, he won’t return for a final match.

Triple H In RAW, 2021Triple H accepts Randy Orton’s challenge: Raw, Jan. 11, 2021 by WWE

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Randy Savage In TNA Turning Point, 2004

In December 2004, after a four-year break from wrestling, Randy Savage returned to the ring at TNA’s Turning Point event. He teamed up with AJ Styles and Jeff Hardy to face Jeff Jarrett, Kevin Nash, and Scott Hall, collectively known as the Kings of Wrestling.

Randy Savage Macho Man Randy Savage Debut at TNA: Victory Road '04 (360p)ᴴᴰ by MrTheTOKidV4

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Randy Savage In TNA Turning Point, 2004 (Cont.)

Despite the star power, the match faced challenges due to the participants’ varying ages and some typical TNA organizational issues, which led to a performance that didn’t quite meet expectations. Nevertheless, Savage’s team emerged victorious, which marked this as his final televised wrestling appearance.

Spider-Man Movies FactsGetty Images

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Bret Hart In RAW, 2011

After making a comeback to the ring in 2010, Bret Hart participated in a number of WWE matches that had little significance and were hardly matches because of his incapacity to withstand blows or severe punishment.

Bret Hart In RAW, 2011Raw - John Cena & Bret Hart vs. Alberto Del Rio & Ricardo Rodriguez by WWE

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Bret Hart In RAW, 2011 (Cont.)

In 2011, he teamed up with John Cena to face Alberto Del Rio and Ricardo Rodriguez in a rushed comedy tag bout on RAW, which was his last match. This was not an ideal way to sign off on a legendary career for Hart.

Bret Hart In RAW, 2011Raw - John Cena & Bret Hart vs. Alberto Del Rio & Ricardo Rodriguez by WWE

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Ultimate Warrior In NWE, 2008

A decade after his last match in June 2008, the Ultimate Warrior returned to wrestling in Barcelona, Spain. He faced Orlando Jordan for the Nu-Wrestling Evolution (NWE) Heavyweight Championship. Despite his efforts, the match was slow-paced. Warrior appeared fatigued and struggled to keep up. 

Ultimate Warrior In NWE, 2008Ultimate Warrior vs Orlando Jordan Full Match ! by UltimateWarriorRules

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Ultimate Warrior In NWE, 2008 (Cont.)

He managed to win the title but immediately vacated it, which marked this as his final wrestling appearance. Fans were excited to see him again, but many felt the match didn’t live up to expectations. The match demonstrated the challenges of returning to the ring after a long absence.

Ultimate Warrior In NWE, 2008Ultimate Warrior - Promo 2008 by G0L0B

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Andre, The Giant In AJPW, 1992

In December 1992, despite ongoing health challenges, Andre the Giant participated in his final wrestling match with All Japan Pro Wrestling. He teamed up with Giant Baba and Rusher Kimura to face Haruka Eigen, Masanobu Fuchi, and Motoshi Okuma. 

AndreAndre The Giant & Giant Baba & Dory Funk Jr. vs. Kawada & Kobashi & Kikuchi (March 4, 1992) by ClassicsPuro83

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Andre, The Giant In AJPW, 1992 (Cont.)

By this time, André’s health had significantly declined, making it difficult for him to move in the ring. Fans found it hard to watch their beloved icon in such a state, which marked a poignant end to his legendary career.

Andre The GiantAndre The Giant & Giant Baba & Dory Funk Jr. vs. Kawada & Kobashi & Kikuchi (March 4, 1992) by ClassicsPuro83

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Lita In Survivor Series, 2006

At Survivor Series 2006, Lita had her final WWE match against Mickie James but didn’t receive a respectful farewell. Instead, Cryme Tyme mocked her retirement by auctioning her belongings. This segment was intended for humor but was widely criticized for its disrespectful nature. 

Lita In Survivor Series, 2006Mickie James vs. Lita (Lita's last Raw Match) by Silverbolt100

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Lita In Survivor Series, 2006 (Cont.)

Lita herself expressed discomfort with the angle. She also approached WWE management, including Vince McMahon, to voice her objections. However, her concerns were dismissed. Moreover, she remarked that she was super uncool with this behavior. 

Lita In Survivor Series, 2006Super Festivals from Ft. Lauderdale, USA, CC BY 2.0, Wikimedia Commons

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