Ranking WWE's Greatest Retirement Matches Ever Ahead of John Cena vs. Gunther

As an icon of the industry, John Cena deserves a sensational sendoff this weekend, and his upcoming clash with Gunther at Saturday Night's Main Event should deliver on that.

Throughout 2025, Cena embarked on a retirement tour that crossed the globe and saw him break records, make history and remind fans why he belongs in the greatest-of-all-time conversation.

Sting was involved in one of the best booked farewells in pro wrestling history when he and Darby Allin defeated The Young Bucks to retain the AEW World Tag Team Championship.

In WWE, quality retirement matches have been hard to come by over the years, especially with so many legends having their last match without actually knowing it until it was too late.

Injuries have cut countless careers short, but certain Superstars have had the honor of going out on their own terms and giving the audience one last memorable performance in their swan song.

Where Cena vs. Gunther will ultimately rank among WWE's most remarkable retirement matches remains to be seen.

7. Trish Stratus vs. Lita (Unforgiven 2006)

Lita and Trish Stratus were wrestling soulmates from the moment they arrived in WWE in 2000 through to when they both decided to call it quits in 2006. The dates of their debuts as well as their respective retirements were mere months apart.

The two dominated the WWE Women's Championship picture during that period and elevated the division to new heights, specifically when they became the first two women to headline Raw on their own in late 2004.

Thus, when Stratus announced her pending retirement from the ring in the fall of 2006, no one made more sense to serve as her final opponent than Lita.

It was more than just one more round between longtime rivals, though. Lita was the reigning women's champ at the time and the title was on the line. The event emanating from Stratus' hometown of Toronto made the match all the more emotional.

It was the top-notch outing fans had come to expect from them, and in a satisfying swerve, Stratus submitted Lita in the Sharpshooter to win her record-setting seventh women's championship.

Lita's sendoff only two months later at Survivor Series was significantly less ceremonious in comparison, so it was refreshing to see Stratus leave on top and being treated like the legend she is.

6. The Undertaker vs. AJ Styles (WrestleMania 36)

The COVID-19 pandemic had an adverse effect on the pro wrestling industry from the very beginning, including the cancellation of WrestleMania 36 in April 2020.

However, WWE pivoted and decided to not only expand the event to two nights for the first time but also hold it in its own Performance Center with no one in attendance.

The Undertaker vs. AJ Styles was one of many matches impacted by the change, despite it shaping up to be one of the more exciting attractions on the card.

The potential was there for Styles to give 'Taker his best bout in years. Thankfully, that happened anyway, albeit in a much different form than originally expected.

It was announced as a Boneyard match, meaning it would be given the cinematic treatment. Their brawl was smartly structured, had some fun surprises and was drastically different than anything WWE had produced in a long while.

The Deadman reprising his American Badass persona was the cherry on top.

Their match was so well-received that 'Taker later decided it would be his last, even without all of the pomp and circumstance. Considering the circumstances, it was the best retirement match he could have had at that stage of his career.

5. 'Stone Cold' Steve Austin vs. The Rock (WrestleMania 19)

Going into WrestleMania 19, there was zero indication "Stone Cold" Steve Austin would be done as an active competitor following his match with The Rock.

He had just returned to the company shortly prior to the pay-per-view after walking out in the summer of 2002 over creative frustrations. Austin and Rock running it back was nothing new given the vast amount of matches they had against each other dating back to 1997, but their rivalries were always must-see television.

Additionally, there was a story worth telling with Rock finally wanting to beat Austin on The Grandest Stage of Them All.

Rock portraying his heel Hollywood persona gave their 'Mania match a whole new dynamic, and it was easily on par with their other encounters. In the end, The Great One secured the three count on Austin to solidify his superiority once and for all.

It became clear shortly thereafter that Austin's neck issues would no longer allow him to compete and he was aware going into the event that it would be his in-ring retirement.

The Texas Rattlesnake wouldn't wrestle again until his impromptu match with Kevin Owens almost two decades later at WrestleMania 38, where he knocked off KO in his home state of Texas and rode off into the sunset as a winner.

4. Randy Savage vs. The Ultimate Warrior (WrestleMania 7)

The Randy Savage of 1991 was very different to the Randy Savage who won the WWE Championship in 1988. He was fueled by hate but still one of the most colorful and charismatic wrestlers on the roster.

After failing to regain the gold himself, he cost The Ultimate Warrior the prestigious prize at the Royal Rumble. That set the stage for a huge WrestleMania match between the two, and to raise the stakes, it was determined that the loser would have to retire.

Warrior would never be mistaken for being a master technician in the ring, but in high-profile situations, he stepped up his game. It was evident in his outing against Hulk Hogan at WrestleMania 6 and that was again the case when he collided with Savage at WrestleMania 7.

Being the tremendous talent he was, Savage carried Warrior for a majority of the matchup, but to his credit, Warrior managed to hold his own as well. It wasn't so match the action that was focal point but rather the story they were telling with neither man willing to give up their legendary careers so easily.

When multiple elbow drops weren't enough to put Warrior away, Warrior battled back and emerged victorious, emphatically placing his foot on top of Savage to earn the honor of ending his career (for a short time, anyway). Macho Man and his long-time lover Elizabeth reuniting afterward was an all-timer of a moment as well.

3. Ric Flair vs. Shawn Michaels (WrestleMania 24)

In November 2007, Ric Flair announced on his return to Raw that he would never retire, only for Mr. McMahon to interrupt and inform him that he would be forced to hang up his boots for good the next match he lost.

Every match that followed for Flair was career-threatening, leading to a string of memorable matchups with the likes of Randy Orton, Triple H, MVP and Mr. Kennedy. The most monumental one of them all came at WrestleMania 24 against Shawn Michaels.

The two had waged war before but never on a stage quite like The Show of Shows.

The predictable outcome that didn't make the story they told any less captivating. Flair fought with everything he had left in him even at 59, while HBK refused to hold anything back.

When it came time to put "Old Yeller" out to pasture, Michaels lived up to his Heartbreak Kid nickname by uttering five devastating words to the newly-inducted WWE Hall of Famer: "I'm sorry. I love you."

One Sweet Chin Music later and Flair's iconic career was over. He'd do damage to his legacy by coming out of retirement for a run in TNA the next year, but his WrestleMania sendoff was exceptionally executed.

2. Triple H vs. Cactus Jack (No Way Out 2000)

Few heels were hotter at the onset of 2000 than Triple H, who took pleasure in inflicting pain on his opponents and running rampant on the entire roster.

Mick Foley, ever the underdog, refused to fall back in line and instead took the fight to the ruthless WWE champion.

Foley fell short to Triple H in a Street Fight at the Royal Rumble yet was granted one last shot at his WWE title at No Way Out the following month, only if he put his career on the line in return.

The Hardcore Legend agreed to the stipulation knowing full well he had the experience advantage over The Game inside Satan's Structure.

Foley underestimated his adversary, as Triple H went to the extreme in order to put him away by resorting the heinous tactics and going so far as to put him through the ring mat. The match was bloody and brutal, and although Foley showed incredible heart, The Game was simply the better man on this night.

It was a beautiful farewell for Foley, who would regretfully return to action a mere six weeks later in time for a Fatal 4-Way main event at WrestleMania 2000.

1. Shawn Michaels vs. The Undertaker (WrestleMania 26)

Shawn Michaels' in-ring return at SummerSlam 2002 against Triple H was intended to be a one-off, but because he fared so well inside the squared circle, he came back for another match at Survivor Series. One more run turned into eight more years.

In that time, he contested classics with John Cena, Chris Jericho and Kurt Angle, but The Undertaker was perhaps his most pivotal. Michaels' devastating loss to The Deadman at WrestleMania 25 nearly drove him into an early retirement, but before he could hang up his boots for good, he had to prove to himself one last time he could beat 'Taker when it mattered most at WrestleMania.

Undertaker's one caveat for the contest was that HBK's career would end if he beat him for the second straight year. It was a risk Michaels was willing to take if it meant getting another crack at the Streak.

However, Michaels' valiant effort against The Phenom was again unsuccessful.

The match itself a gem, and what what made it more special was that Michaels did remain retired for many years. His one-off return at Crown Jewel 2018 alongside Triple H to take on The Brothers of Destruction is best forgotten, as nothing may ever come close to how perfect his original farewell was.