WWE superstars are signed to ironclad contracts, but sometimes the stars decide that it's their time to step away from the company. Retirement matches are always painful to watch since one of the stars could well leave the company following the pinfall, but most of the time these stipulations are used as a way to raise the stakes in the match.
Over the past few years, these match stipulations have been reserved for some of the biggest rivalries and have seen some of WWE's biggest stars walk away from the company as a result. Many times it has also seemed as though stars would leave, then they shockingly got the win and managed to hold on to their contracts.
The stipulation always adds excitement to a feud that couldn't possibly end any other way and it also gives fans a reason to get behind their favorite superstar, which is always a good thing as a wrestling fan.
There have been many matches that have either been stipulated as career-ending matches or actually ended someone's career because of an injury or an accident in the match. The following are the most memorable ones from the past few decades.
15 Seth Rollins vs Sting
Though Seth Rollins has only been in WWE for around four years, he has developed himself a reputation as a "dangerous wrestler." This could have to do with the fact that three wrestlers were injured while he was in the ring with them, or because a WCW Legend was amongst them.
When Rollins and Sting met at Night of Champions back in 2015, it wasn't supposed to be Sting's final match but a "bucklebomb" from the World Champion gave Sting whiplash and caused him a whole array of neck problems that has kept him out of a WWE ring ever since.
14 Triple H vs Brock Lesnar
It was one of the biggest feuds of the year heading into WrestleMania 29 and decided to up the game in their SummerSlam 2012 rematch by putting Triple H's career on the line. The duo had already brawled all over the arena and let each other battered and bloodied, but adding a career-ending stipulation was a master stroke.
WrestleMania 29 was a great year for WWE with CM Punk and The Undertaker stealing the show, but Triple H and Brock Lesnar definitely played their part in making it a stand out WrestleMania event. Triple H won the match and retained his career, luckily otherwise there would be another COO in WWE right now.
13 Goldberg vs Bret Hart
Another addition to the list that was not supposed to be the final match for Bret Hart when he was down to face Goldberg at Starrcade in 1999, but it did end up marking the end of Hart's full-time wrestling career.
Goldberg carelessly mule kicked Hart in the head during the match which resulted in a severe concussion. Hart later hit his head on the concrete floor as well, which added to many other injuries that he had suffered that day which later gave him Post-Concussion Syndrome, something that he has blamed Goldberg for ever since.
12 Lita vs Mickie James
It was literally weeks after Trish Stratus retired from the WWE in her hometown of Toronto, Canada at Unforgiven 2006 when it was decided that her long-time friend and rival Lita would follow her out of the exit door.
Lita was a four-time Women's Champion and a very talented wrestler, and she deserved a much better send-off than WWE gave her. Not only was she defeated by Mickie James and lost her Women's Championship in her last match, but Cryme Tyme then came out and had a "Ho Sale" as a way to further embarrass Lita. The match itself was incredible and was one of the best Mickie and Lita had ever had, so that's why it deserves a place on the list.
11 Edge vs Alberto Del Rio
It was one of the stand-out matches of WrestleMania 27 and it has only been made more special by the fact that it will always be known as Edge's final WWE match. Following his incredible title defense on the grandest stage of them all, Edge was given some bad news.
Edge was diagnosed with Cervical Spinal Stenosis, which means that if he continued to wrestle or took a bad bump in the ring then he would be paralyzed. Edge decided against taking the risk and retired from WWE, vacating the Championship in the process. It truly was a fantastic match for The Rated R Superstar to end on.
10 AJ Lee vs Kaitlyn
AJ Lee and Kaitlyn shared a friendship and a bond that is rare between WWE Superstars, they met in FCW and climbed the ranks in NXT together before being part of the biggest female rivalry at the time, over the Divas Championship.
After Kaitlyn had dropped the Divas Championship to AJ, she decided that she didn't want to be in WWE anymore and asked for a release to pursue other avenues of employment. She asked to have her final match against AJ and the two hugged following the match in true Kaitlyn and AJ style.
9 Triple H vs Cactus Jack
No Way Out back in 2000 saw one of the most brutal retirement matches of all time as Triple H and Cactus Jack collided inside Hell in a Cell. The rivalry between the two stars had reached boiling point and this showed throughout the match when it seemed that they wanted to rip each other apart.
The match ended when Triple H back body dropped Mick Foley off the top of the cell and through the ring below. Triple H then hit a Pedigree to send a message and signal the end of Cactus Jack's career. Of course, Mick Foley has returned since then and is currently the General Manager of Monday Night Raw.
8 Tommy Dreamer vs Zack Ryder
Every diehard ECW or WWE fan will be able to tell some incredible stories about Tommy Dreamer, he was one of the best ECW Legends of all time and when ECW was revamped back in 2005, it was obvious that Tommy would get the call.
Dreamer's career in WWE didn't last long since he was part of the New Breed vs The Originals and William Regal forced him to put his career on the line in a match with Zack Ryder. "The Long Island Iced Z" shockingly picked up the win over Dreamer and the hardcore superstar was released from his WWE contract the following year.
7 Trish Status vs Lita
Trish Stratus was a seven-time Women's Champion and is widely considered to have been one of the best female wrestlers in WWE history, so when she announced her retirement from WWE in 2006, WWE had to let her walk away in style.
Trish decided to retire in her hometown of Toronto, Ontario, Canada at Unforgiven back in 2006. She faced Lita for the Women's Championship and won it for the seventh time before vacating it and walking away from the company a few hours later. What is also worth noting is that Trish won the move with the Sharpshooter, a submission move made famous in Canada, and one that she hadn't used up until this final match. It was the perfect last match between two of the best female wrestlers of all time.
6 CM Punk vs John Cena
This was supposed to be the final match of CM Punk's WWE career, Punk had promised that he would win the WWE Championship at Money in the Bank in 2011 and he would leave WWE with the title as well.
Punk did win the Championship and he did run through the crowd and exit the arena afterward, but Punk had already signed a new WWE contract before he walked away from WWE, which meant that he had to come back. Even so, John Cena and Punk put on the match of their lives and it was one of the best matches that year. Punk did return to WWE a week later, though, with a new theme and his title, but since Cena had already won the title again at that point, they then faced off at SummerSlam as well.
5 Michelle McCool vs Victoria
Victoria was an incredibly gifted female performer, but since Trish Stratus and Lita were always the main focus of the Women's Division, it seems that Victoria never got a fair chance during her time in WWE. That being said, she is still a former WWE Women's Champion and was part of some of the best moments in WWE history.
The Widow's Peak Freak's retirement came out of the blue. She lost her match to Michelle McCool on an episode of SmackDown and then thanked the crowd and emotionally said her goodbyes to a company that she had given her all for many years. She later moved over to TNA where she continued to impress inside the squared circle.
4 Jeff Hardy vs CM Punk
Jeff Hardy and CM Punk had a fantastic feud back in 2009 that culminated in Punk winning the WWE Championship from Hardy at Tables, Ladders, and Chairs. This didn't sit well with Hardy and he decided to put his career on the line in a steel cage match on an episode of SmackDown.
Hardy lost the match and per the stipulations, he was forced to leave WWE as well. He gave an emotional speech following the match about how Matt Hardy was still there and that he would be back some day, before walking up the ramp and once again being taken out by CM Punk. It was reported that Hardy was released because he had failed his third WWE Wellness Policy test.
3 Dolph Ziggler vs The Miz
The most recent entry on the list and rightfully at number three, back in 2016 Dolph Ziggler's career was going nowhere, he was reduced to being a mid-card talent and forced to job out to NXT stars coming up to the roster.
He decided that he wanted the Intercontinental Championship and after already failing to capture it weeks before, Ziggler put his career on the line and stated that if he didn't defeat The Miz then he would walk away because he had nothing left. Many fans believed that Ziggler was going to leave and were shocked when Dolph lifted the Championship at No Mercy and managed to retain his career. He did, however, lose the title back to Miz not long after, but that doesn't take away from how incredible this match really was.
2 Shawn Michaels vs Ric Flair
It was definitely one of the more emotional retirement matches as Ric Flair took on Shawn Michaels at WrestleMania 24. Vince McMahon told Ric that the next match he lost would be his last, and in true Flair style, he decided to go out with a bang.
Michaels wasn't happy about being the chosen one to end his friend's career, but the duo put on a fantastic show and when Shawn went for the superkick he mouthed 'I'm sorry, I love you' before delivering the final blow that signaled the end of Flair's career. Flair has returned to WWE since, but not in a full-time wrestling capacity, which means that the match still remains his last.
1 The Undertaker vs Shawn Michaels
The rematch from WrestleMania the year before saw Shawn Michaels desperate to prove that he could defeat The Deadman and that if he couldn't then he would walk away from wrestling for good.
True to his word, Michaels was defeated by The Undertaker and the two embraced after the match as Michaels walked away from WWE and he hasn't returned to in-ring competition since. Michaels is one of the only WWE superstars who stated that when he was retired, he was not coming back, and he hasn't.
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