5 best career on the line matches ever in the WWE

Where does this match rank amongst the greatest career on the line matches ever in the WWE?

It is always difficult to say goodbye to someone you love. When it comes to WWE, a number of men and women have come through their doors, faced a number of different challenges, and walked out on their own terms.

It is sad when a wrestler's career is cut short due to injury, but they realise that those risks are part of the business and do it because they love it. How about wrestlers whose careers were in the hands of their opponents?

In a number of different instances, careers have been cut short to help further a storyline, and also to provide a reason why they are saying goodbye.

However, while retirement matches are usually meant to highlight that someone is leaving the company, sometimes it's a way to say ‘Thank you for the opportunity, I'm now going to go home and enjoy the rest of my life with my family.'

In a number of cases, the people that lost these matches did so in a way that they can be proud of. These men and women's lives are held to a different standard because of their body of work, and fans recognise that. Here are the five best career on the line matches ever in WWE.


#5 Trish Stratus vs. LitaUnforgiven 2006

In front of her home crowd, Trish’s career ended with a victory and a seventh WWE women’s championship

It isn't that common for a retirement match to be all that memorable. Yes, those participating are of great significance, and their contributions to wrestling are important, but the match itself is ultimately mostly a send-off and a thank you.

On one particular occasion, a retirement match wasn't only significant because it involved two women, but because it involved two women who have called each other best friends outside the ring. During their time in the ring, Lita and Trish had one of the most exciting rivalries in wrestling.

Also read: 5 WWE Superstars other than Undertaker who could have had a Wrestlemania streak

Lita came into the promotion much more seasoned, but by the end of their careers, it could be said that they mirrored one another.

They were the first women to main event a Monday Night Raw. And on this particular evening, it was already known that Trish was going to be walking away from the ring after the match, regardless of the result.

We say regardless of the result because the WWE Women's championship was on the line, with Lita being the champion. Someone winning the match and retiring was unlikely, but on this night it happened. Trish defeated Lita, capturing her seventh Women's title and went on to retire from professional wrestling.

#4 Shawn Michaels vs. “Nature Boy” Ric Flair Wrestlemania 24

With a tear in his eye, Michaels was prepared to end the career of his idol in Ric Flair

Anyone familiar with Shawn Michaels should be equally familiar with those he has praised for their contributions to wrestling history. Former sixteen-time world champion, ‘The Nature Boy' Ric Flair has often been mentioned as one of the men that Michaels respected the most.

The dirtiest player in the game has in turn called Michaels the greatest athlete he has ever seen. And in Flair's storied career. he has certainly faced the very best in the ring.

When these two WWE Hall of Famers faced one another, we knew that having someone defeat you to end your career is as much a sign of respect as having them defeating you for a championship.

What we were treated to was a match-up of two men whose stamina far surpassed that of men barely half their age, putting on a wrestling clinic.

In the closing moments of the match, Michaels told Flair a staggered ‘I'm sorry. I love you' and proceeded to hit him with sweet chin music, Michaels then pinned Flair for a three count and victory.

As soon as the match ended, Michaels immediately clutched a defeated Ric Flair, showing continued respect for his mentor once again.

#3 Dolph Ziggler vs. The Miz No Mercy 2016

With everything to lose, Ziggler put it all on the line coming out victorious

Their rivalry seemed endless, as Ziggler and The Miz faced one another for what seemed like forever. However, when they met at No Way Out this past year, The Miz had nothing to lose really, but he wanted Ziggler to risk what mattered most to him: his career.

When Ziggler initially asked for one more opportunity at the Intercontinental championship, The Miz said no. Fans really couldn't blame The Miz, as he had beaten Ziggler multiple times previously. There was, however, one thing that changed The Miz's mind.

Ziggler would put his career on the line in exchange for a final opportunity at the championship.

It proved to be a risk that paid off. As it turned out, their match was stellar, as they went back and forth, and even outside interference didn't take away from this being an epic battle.

In the end, Ziggler came out victorious, becoming the Intercontinental champion and saving his career in the process.

#2 Triple H vs. Cactus Jack – No Way Out 2000

A brutal affair is the only way Cactus Jack would have wanted it in his last match against Triple H

One is the hardcore icon and the other is the cerebral assassin. And it seemed as though whenever Mick Foley and Triple H faced each other in the ring, the result was an insanely brutal affair.

After having seen their brawls years earlier, fans were aware that a match between these two would normally see a sledgehammer, a baseball bat wrapped in barbed wire, and potentially thumbtacks. And their match from No Way Out in 2000 proved to be another brutal chapter in their storied rivalry.

This no holds barred contest had the additional stipulation that it’d be a retirement match if Foley lost. The scene was set, as their match was contested in a Hell in a Cell, it saw a number of typical Mick Foley spots take place once again.

At the climax of the match, Triple H back body dropped Cactus Jack through the ceiling of the Cell and finished him by delivering a pedigree. Jim Ross' ended his call of the match by saying ‘You're going to be missed,' as it would ultimately be the end of a career… at least for a few weeks.

#1 Shawn Michaels vs. The Undertaker Wrestlemania 26

Michaels put it all on the line in his match against The Undertaker

If one match went above and beyond when it came to creating a story and delivering a poignant climax, it has to be the Shawn Michaels vs Undertaker match from Wrestlemania 26.

These two had storied matches before, with one match actually seeing Michaels suffering an injury that caused him to step away from the ring for nearly five years.

However, time passed and Michaels recuperated, and thus he was able to have a match against the Undertaker that didn't simply tell the story of the streak being challenged by a career. It was a battle of two men that were as key to the success of the WWE during the Attitude era as anyone else.

The match came on the heels of the previous year's epic battle, which Michaels had lost, becoming simply another number in the Undertaker's Wrestlemania winning streak. This match provided fans with near pinfalls, epic dives and some of the most memorable moments ever seen during the Undertaker's streak.


Send us news tips at [email protected]

Do you love to play crosswords, Wordle or other exciting games? We'd like to connect with you. Fill the form here!

Quick Links

App download animated image Get the free App now