What These Iconic Wrestlers' Final Matches Were Really Like

Like all things, pro wrestling careers have beginnings and endings. Not every wrestler gets the chance to choose how they'd like to go out, but on occasion, some of the greats get the opportunity to hang up their boots with pride. These swansongs are often some of the year's biggest matches and are accompanied by intense emotion and thrilling callbacks to the wrestler's greatest moments.

Recently, one of the most recognizable wrestlers and arguably the biggest star to walk out of WCW, Sting, hung up his boots after nearly 40 years in the industry. The final match included an interesting reference to his past, and unlike many of the other entries on this list, "The Icon" went out on top and retired as a champion. His final match seemed to treat him with dignity and allowed him enough time to say farewell. However, not all final matches were as well received as Sting's, and even one of his closest friends had a bout that many would rather forget.

Another man who accompanied "The Icon" to the end, Ric Flair, had what many recall as one of the most emotional retirement matches — even though he'd essentially undo it a few years later in his controversial "Ric Flair's Last Match" event. However, Flair and Sting aren't the only two who have called it quits in the ring, and their farewells were far better put together than some of the others on this list.

Randy Savage vs. The Ultimate Warrior at WrestleMania VII

"Macho Man" Randy Savage is fondly remembered as one of the most charismatic stars of his generation. He captured gold numerous times in his WWE career and later found further success in WCW. Despite all his success, Vince McMahon forced Savage to retire in 1991, leading to his WrestleMania VII match against The Ultimate Warrior.

The two men started the bout with a pose-off to try to win over the crowd, but it quickly turned to action. Sensational Sherri also got involved in the match to give Savage the upper hand. The two veterans went back and forth until they reached a barricade spot, which swung momentum firmly into Warrior's lap. Eventually, he hit two running shoulder blocks onto Savage and pinned him in the middle of the ring with his foot on his chest.

Savage worked the remainder of his contract and was forced to retire. However, this didn't last, and McMahon reversed his decision before Savage went to WCW, where he proved the former WWE boss wrong and revitalized his character for some time. Because of his WCW run, fans have likely forgotten about this match, and luckily for Savage, it wouldn't be the last time he'd ever step into the ring.

Stone Cold vs. The Rock at WrestleMania XIX

"Stone Cold" Steve Austin was arguably the face of the Attitude Era during a time when the roster was packed with some of the biggest names in the industry. Austin went toe-to-toe with the best, but unfortunately, while he wasn't old even for an athlete, he couldn't continue pushing himself due to injuries. Austin knew WWE WrestleMania 19 would be his final match, and with The Rock as his opponent, it was against someone he knew well.

People still praise the build-up to the match online. The Rock had recently returned to WWE as his "Hollywood" persona and began noting how he'd done nearly everything in the industry except beat Austin at WrestleMania. The two had fought at two earlier 'Manias, but Rock wanted to settle the score and sent out the challenge. Austin accepted.

The bout itself included many spots where both men pushed the rules and tried to strangle the other. However, in typical heel fashion, The Rock continuously targeted Austin's knees and even used the Sharpshooter in an attempt to get a submission victory. Austin hit back later in the match by stealing The Rock Bottom and getting a two-count. Unfortunately for Austin, he ate a Stunner from "The People's Champ." Things became heated by the bout's end, but The Rock won after hitting three Rock Bottoms.

For years, this was the heartwrenching end to "Stone Cold's" career. However, he ultimately returned to the ring at WrestleMania 38, where he defeated Kevin Owens in a no-holds-barred match.

Trish Stratus vs. Lita at Unforgiven 2006

Trish Stratus is one of the most accomplished women of her generation. She captured gold multiple times at a time when women had far fewer opportunities in wrestling than they do today. Despite her success, even Stratus had to eventually step away from the industry, and in 2006, she ended her active career and stepped back.

During her career, one of her ongoing rivals was undoubtedly Lita, another legendary figure in women's wrestling. Naturally, there was no better opponent to end this chapter of her career, and the two women went toe-to-toe in Stratus' hometown during 2006's Unforgiven. The two women became physical within the opening moments of the match. After some back-and-forth brawling, Lita missed a moonsault, giving Stratus a crucial two-count. The match became more heated afterward, but Stratus couldn't keep Lita down — the Stratusfaction couldn't even give her the victory. Ultimately, it took a Sharpshooter to end the match, allowing Stratus to finish her career in her hometown to huge applause.

Despite this being her retirement bout, Stratus returned to the ring two years later when she teamed up with John Cena to take on Beth Phoenix and Santino Marella. Since then, Stratus has returned to write the final chapter of her WWE career, most recently feuding with Becky Lynch and proving that she still has plenty of gas left in the tank.

Ric Flair vs. Shawn Michaels at WrestleMania XXIV

"The Nature Boy" Ric Flair is considered by many to be one of the greatest to ever step into the ring, largely due to his character work. Over his lengthy career, Flair faced some of the best in the industry, but by 2007, he had probably accomplished everything he could at that point. However, Flair disagreed. In a promo addressing his home crowd of Charlotte, North Carolina, he turned what many believed to be a retirement speech into a passionate declaration that he would never retire and would only stop once he died in the ring. Unfortunately for Flair, Vince McMahon pushed "The Nature Boy" to his limit and stipulated that a single defeat would mean the end of his career.

Despite getting a few wins, Flair eventually came face-to-face with Shawn Michaels. The two clashed at WrestleMania XXIV, where they pushed the other to his limit. Despite his age, Flair took a beating from Michaels and just kept going, walking off massive moves like a moonsault from the turnbuckle to the outside apron, figure-four Leglock, and a Sweet Chin Music.

This led to an emotional exchange between the two wrestlers. Flair, finally at his limit, could barely stand on two feet while Michaels was in the corner winding up for one more Sweet Chin Music. Flair struggled toward Michaels with tears in his eyes, while his opponent mouthed, "I'm sorry, I love you," before hitting the final kick. For years, this was regarded as one of the most beautiful swansongs in the industry — until Flair joined TNA and wrestled more matches.

The Ultimate Warrior vs. Orlando Jordan at Nu-Wrestling Evolution

The Ultimate Warrior was one of the most popular stars of his generation, and notably one of the biggest merch pushers at the height of his career. Despite this, his ability in the ring has been criticized by some of his peers and even fans online. However, this never took away from his status as a legend, leading to his WWE Hall of Fame induction shortly before his sudden passing.

Warrior's final WCW match was at WCW Halloween Havoc 1998, where he faced Hulk Hogan. Before that, his last recorded WWE match was against Owen Hart during a "WWF Raw" taping. However, in 2008, he put on the face paint and donned his signature attire one last time in a match against Orlando Jordan at Nu-Wrestling Evolution (NWE). In front of a crowd of 15,000 people in Spain, Warrior went to war with Jordan for the promotion's NWE Heavyweight Title. Even in his prime, Warrior wasn't known for his stamina, and this match was no different. Warrior showboated his way through spots, which Jordan set up nicely for the aging veteran. After two lariats and a shoulder block, Warrior defeated Jordan and captured the NWE Heavyweight Title. However, instead of walking off with the belt, he thanked Jordan and returned the belt to the promotion.

Unlike the others earlier in this list, Warrior never walked back his retirement — perhaps because he never had the chance to — and didn't hang up his boots in a promotion close to the size of the WWE.

Shawn Michaels vs. The Undertaker at WrestleMania 26

A few years after retiring Ric Flair, Shawn Michaels put his career on the line in a WWE WrestleMania feud that has been highly praised by many. Michaels closed off his career as an active wrestler at WrestleMania 26 after a second failed attempt to end The Undertaker's undefeated streak at the "Show of Shows."

While their story ended in 2010, the foundations were laid during 2007's Royal Rumble, which saw the two veterans as the last two men standing. After a 10-minute bash, Undertaker walked away with the victory, but the heat between them wouldn't end there. The two men came to blows again during WrestleMania 25, which iconically portrayed Michaels in a white jacket and hat to mirror Undertaker's dark gimmick. 

The match allegedly exceeded their time limit, but Vince McMahon urged production to allow the two to continue, leading to an epic clash. However, despite failing to beat Undertaker, he wanted one more match. Unfortunately for Michaels, "The Deadman" had enough. This pushed Michaels over the edge, and he became desperate to get 'Taker's attention. In the end, Undertaker relented, and the veterans went head-to-head again.

Despite a valiant effort, Michaels went down after The Undertaker hit him with a jumping Tombstone piledriver, ending the career of "The Showstopper" — until Crown Jewel 2018, when a bald Michaels teamed up with Triple H to take on the man who retired him, The Undertaker, and Kane. Sadly, the match has been highly panned, and many fans still choose to believe that Michaels retired at WrestleMania 26.

Antonio Cesaro Vs William Regal at NXT

While William Regal never captured a World Championship in WWE, his character work and in-ring ability have been praised by his peers and fans. Regal is additionally known for his many on-screen authority figure roles and even formed the Blackpool Combat Club faction during his brief stint with AEW.

Despite being a part of the main roster, Antonio Cesaro — who now goes by the name Claudio Castagnoli — occasionally competed on "NXT" and was set to face Regal. In a promo ahead of the match, Regal claimed he had been looking back at his legacy and admitted that his career was nearing its end. He claimed he had failed ambitions to capture a World Heavyweight Title, but since he was set to compete against Cesaro, he praised "The Swiss Superman" and said that it would be an honorable way to end his career.

The match between the two was a technical exhibition, with both men targeting one another's weaknesses. However, Cesaro's athletic advantage was prevalent, leading to him dominating the much older Regal. Despite his advantage, Cesaro didn't relish the final moments of the match, when he knew one final move would end the bout and his opponent's career. Even after the victory, Cesaro didn't seem to find any pleasure in winning.

Over the years, both Regal and Castagnoli have shared their thoughts about the match on social media. That said, while he retired his character in the "NXT" match, Regal wrestled Sami Zayn in a Crossfit gym in Dubai afterward.

Batista vs. Triple H at WrestleMania 35

Batista started his wrestling career much later than his peers but quickly rose to the top after joining the Evolution stable, which included Triple H, Randy Orton, and Ric Flair. After the stable imploded, both Orton and Batista went on to become two of the biggest stars of their generation.

After a hiatus from WWE to embark on a Hollywood career, "The Animal" returned and entered a feud with Triple H. The pair had some build-up toward the match, most notably with a promo in which Batista constantly said, "Give me what I want," to the point that the clip has become a meme. Nevertheless, the two were set to go head-to-head in a no-holds-barred match at WWE WrestleMania 35, where Triple H's career was interestingly on the line and not Batista's.

Early in their match, the two men took things to the extreme and clashed outside the ring. This led to a spot where Triple H choked Batista with a chain. The onslaught didn't stop there, as Triple H then used pliers on Batista's fingers and ripped his nose ring out. "The Animal" ultimately regained some momentum and ended up slamming "The Game" through an announce table. At this point, the fans were still thrilled.

Later in the match, Triple H brought out his signature sledgehammer but was met with a spear from Batista. After a scuffle, "The Animal" hit his Batista Bomb for a two-count. Unfortunately, fans began to lose interest in the match at this point. By the end, Triple H had to hit two separate Pedigrees to keep Batista down. Following the match, Batista announced his retirement, and this became Triple H's final WrestleMania to boot.

The Undertaker vs. AJ Styles at WrestleMania 36

The Undertaker had a wrestling career that many could only have hoped for. After becoming a multi-time champion, winning many accolades, and going through many gimmicks, "The Phenom" finally hung up his boots for good at WWE WrestleMania 36 following a cinematic Boneyard match. For his final opponent, 'Taker chose AJ Styles as he reminded him of Shawn Michaels.

Leading up to the feud, both men used one another's real names and took various jabs at each other's families. Regarding the match, Styles made a grand entrance and jumped out of a casket, mocking his opponent. However, The Undertaker wouldn't let this outshine him, as he entered on a motorcycle and reverted to "American Badass*" gimmick. 

The rest of the match was like a movie, allowing 'Taker to sidestep all the physical limitations his 55-year-old body had picked up after decades. Styles held firmly onto the momentum at one stage in the match, attempting to bury 'Taker. However, "The Deadman" still had some supernatural powers left, resulting in him teleporting behind Styles and gaining back the momentum. In the end, The Undertaker stood tall after burying Styles instead.

Not too long after, Mark Calaway finally shed his gimmick and presented himself to the world as the man who played The Undertaker for decades. The match has also been praised by many for Taker's performance and Style's willingness to put over "The Phenom" one more time. At the time of writing, Calaway hasn't broken his retirement — yet.

Sting and Darby versus The Young Bucks at AEW Revolution

Sting impressed most of his fans and former peers during his AEW run. Despite being well into his 60s, "The Icon" proved that he could still keep up with the young talent and often pushed his body by performing death-defying stunts. Unfortunately, like the rest of this list, even Sting couldn't wrestle forever. In 2023, Sting announced that AEW Revolution 2024 would be his final match, thus beginning the buildup to his swansong. Many believed his final match would be a singles bout, potentially against Darby Allin. Instead, they captured the AEW World Tag Team Championships and entered a feud with The Young Bucks.

In the final "AEW Dynamite" before their clash, Sting recreated his iconic WCW entrance, descending from the rafters to save Ric Flair and Allin from an attack by Matthew and Nicholas Jackson. The fanfare continued once the actual match took place, with "The Icon" walking out along with his sons dressed as two iterations of his gimmick, "Surfer Sting" and "Wolfpac Sting." Naturally, the match included many spots, with Allin taking a plunge off a ladder from the inside of the ring through a pane of glass.

At one point in the match, Sting even faced The Bucks all by himself, and despite them pushing him to his limit, he outsmarted both. Another memorable spot occurred when the Borden brothers, Allin and Sting, each hit the Bucks with the Stinger Splash and a Coffin Splash — in Allin's case — leading to "The Icon" putting both Bucks in the Scorpion Deathlock and getting the win. In the end, Sting retired as a champion.