WWE has a long history of career-ending matches, and some of the most emotional moments in wrestling have come when a legend steps into the ring for the last time. Whether it’s a beloved superstar being forced into retirement or an icon choosing to walk away on their own terms, these matches leave a lasting impact. Fans witness decades of dedication coming to an end, making these bouts unforgettable.
Some of these moments have been filled with mutual respect, while others have been heartbreaking betrayals. No matter the circumstances, the emotions are always raw. From final goodbyes to stunning farewells, these matches aren’t just about wins and losses—they’re about legacies. Here are four of the most emotional WWE PPV matches that marked the end of a legendary career.
1. Shawn Michaels vs. The Undertaker – WrestleMania 26 (2010)
The Undertaker vs. Shawn Michaels (Image via Getty)Few retirement matches have been as emotionally charged as Shawn Michaels’ last stand at WrestleMania 26. Two of WWE’s greatest performers faced off in a Streak vs. Career match, where Michaels put everything on the line against The Undertaker’s undefeated record.
Michaels had previously pushed The Undertaker to the limit at WrestleMania 25, delivering one of the best matches in history. A year later, he was determined to do it again, but with even higher stakes. The bout was a masterclass in storytelling, filled with high-risk moves, near falls, and unforgettable moments. The crowd was on the edge of their seats as Michaels desperately tried to break the streak.
In the final moments, a defiant Michaels slapped The Undertaker, refusing to go down without a fight. The Deadman responded with a thunderous Tombstone Piledriver, sealing the victory and ending Michaels’ career. After the match, an emotional Michaels waved goodbye to the WWE Universe, walking away after an unmatched career. It was a farewell that left fans with tears in their eyes, knowing they had just witnessed the end of an era.
2. Ric Flair vs. Shawn Michaels – WrestleMania 24 (2008)
Shawn Michaels vs. Ric Flair (Image via Getty)This match wasn’t just about winning or losing—it was about saying goodbye to one of the greatest of all time. Ric Flair had built a career spanning decades, and at WrestleMania 24, he put it all on the line against Shawn Michaels in a Career-Threatening Match. The stipulation was simple: if Flair lost, he had to retire.
The match itself was a blend of old-school storytelling and deep emotional investment. Michaels, a longtime admirer of Flair, struggled with the idea of being the one to end his idol’s career. Flair, on the other hand, fought like a man who refused to quit. The crowd watched in anticipation as the two legends exchanged moves, with Flair pulling out every trick in his book to stay alive.
In the final moments, Michaels hesitated before delivering his iconic Sweet Chin Music. With tears in his eyes, he mouthed the words, “I’m sorry. I love you.” before landing the decisive kick. Flair fell to the mat, and Michaels pinned him, bringing an end to the Nature Boy’s legendary career. As Flair stood in the ring, overwhelmed with emotion, the crowd showered him with admiration, giving him the farewell he deserved.
3. Triple H vs. Batista – WrestleMania 35 (2019)
Triple H vs. Batista (Image via Getty)This match had everything—personal history, brutality, and a final chapter for one of WWE’s biggest stars. Batista returned to WWE in 2019 with one goal: to end Triple H’s career. The two had a storied past, dating back to their days in Evolution, but this time, it was all about proving who was truly the best.
The stakes were high. If Triple H lost, he would be forced to retire. What followed was one of the most physical matches in WrestleMania history. From steel chains to pliers ripping out Batista’s nose ring, it was a brutal war that pushed both men to their limits. The No Holds Barred stipulation allowed them to take their aggression to the extreme, making it an unforgettable battle.
As the match neared its climax, Ric Flair made a surprise appearance, handing Triple H his signature sledgehammer. One final shot with the weapon put Batista down for good, allowing The Game to pick up the victory. This loss marked the end of Batista’s in-ring career, and he later confirmed his retirement from wrestling. It was a fitting end for a man who had been a dominant force in WWE for years.
4. Kurt Angle vs. Baron Corbin – WrestleMania 35 (2019)
Kurt Angle vs. Baron Corbin (Image via Getty)Kurt Angle’s retirement match was meant to be a celebration of his incredible career, but the outcome left many fans heartbroken. As one of the greatest technical wrestlers of all time, Angle had achieved everything there was to accomplish in WWE. When he announced that his final match would take place at WrestleMania 35, fans hoped he would face a legendary opponent. Instead, WWE chose Baron Corbin.
Many were disappointed by the choice, believing Angle deserved a higher-profile farewell. Despite that, Angle gave everything he had in his final match. He showcased glimpses of his former greatness, hitting suplexes and locking in the Ankle Lock. However, Corbin proved to be too much for the veteran, landing the End of Days to secure the victory.
After the match, Angle addressed the crowd, thanking them for their support throughout his career. It wasn’t the fairy-tale ending many had hoped for, but it was a moment filled with emotion. As Angle left the ring for the final time, the WWE Universe showed their appreciation, giving him the send-off he had earned through years of dedication.
A Legacy Beyond the Ring
Career-ending matches in WWE are more than just the end of a storyline; they mark the closing chapter of a superstar’s journey. These moments stay with fans forever, reminding them of the sacrifices, dedication, and passion that these legends poured into the ring. From heart-wrenching goodbyes to final moments, these matches continue to be talked about years later, proving that in WWE, a legacy never truly fades.