Whenever wrestlers reach the stage of being seen as icons they’re typically coming toward the very end of their careers. Anyone who is given such a nickname is often a legend of the business, but in professional wrestling, a lot of people struggle with hanging up the boots, which leads to performances continuing to happen.
At times this can be a good thing, because seeing an icon wrestle is always enjoyable, and when they’re able to perform at a high enough standard still it is entertaining. Unfortunately, there have been times over the years when an iconic wrestler has struggled to perform to the standard expected.
10 Sting (Vs. Seth Rollins – Night Of Champions, 2015)
Sting is someone who is still wrestling at a high level to this day, putting on great performances for AEW whenever he laces up the boots. However, his final match for WWE was a different story as he struggled to perform against Seth Rollins due to suffering a neck injury toward the end of the match.
Sting suffered temporary paralysis, showcasing how serious the situation was, and it created a genuinely scary situation. Nobody wants to see an iconic wrestler hurt, but that is what happened in this one, with Sting simply being lucky he could walk again, let alone still wrestle.
9 Goldberg (Vs. The Undertaker – Super ShowDown, 2019)
Goldberg facing The Undertaker was a dream match for fans that unfortunately happened 10 years too late to create something entertaining. Both men were past their best when this one took place, with Goldberg in particular looking off from the first bell to the last.
This is because he concussed himself by headbutting his door to get ready for the match backstage. It led to him being all over the place in the match which led to some dangerous spots taking place where both men could have ended up being legitimately hurt.
8 Ric Flair (Vs. Jay Lethal & Jeff Jarrett, Ric Flair’s Last Match)
Ric Flair has seemingly ended his career several times, but at the age of 73, he decided to lace up the boots one more time for an event branded all about it being the end for him. Despite having several severe health complications the Nature Boy stepped back into the ring to team up with Andrade El Idolo against Jay Lethal and Jeff Jarrett.
While the other three men looked good, it was very clear that Flair was past his best and shouldn’t have been put in that situation. He has since admitted to blacking out a couple of times during the match as well, which was concerning for people to hear.
7 Jeff Hardy (Vs. Ethan Page & The Gunns, Double Or Nothing, 2023)
Jeff Hardy is someone who has put his body on the line throughout his entire career, taking some of the most insane bumps in wrestling history. That has taken an obvious toll on his body because Hardy is unfortunately moving a lot slower nowadays whenever he gets into the ring.
That was very clear during a six-man tag team match at Double Or Nothing in 2023 when Hardy looked rusty. His movement was off and he even slipped from the top rope during a Whisper In The Wind attempt, which made his performance even more glaring.
6 The Rock (Vs. John Cena – WrestleMania 29)
The Rock competing against John Cena is one of the biggest matches in WWE history, and while this was the rematch it still drew in huge numbers and a lot of attention from outside of the wrestling bubble. Unfortunately, The Rock suffered a torn abductor and abdominal muscles as well as a hernia during the match.
While the People’s Champion gritted his teeth and fought through the situation, he wasn’t able to deliver the performance he would’ve wanted. It limited the match and what he could do, but the fact he was able to finish it was a credit to him.
5 Triple H (Vs. Brothers Of Destruction – Crown Jewel, 2022)
DX facing Brothers Of Destruction is a true dream match for most people considering the sheer amount of star power involved here. However, it ended up being a memorable match because of how disastrous it ended up being, as nobody came out of this one looking good.
Triple H was the one who truly struggled to perform throughout this one though because he sustained a pectoral injury during this match. He had to finish this on the sidelines due to having a legitimate issue, which summed up this match perfectly.
4 Shane McMahon (Vs. The Miz – WrestleMania 39)
Shane McMahon might not have been a full-time wrestler at any point in his career, but he is someone who is beloved by fans due to the risk-taking style he provides. He made a surprise return to WWE at WrestleMania 39, which was a huge moment as he received a major pop.
It was supposed to create an impromptu match against his former partner and rival The Miz, but it ended in disaster. McMahon tore his quad in the middle of the ring, bringing an end to things in the worst possible way.
3 Bret Hart (Vs. Vince McMahon – WrestleMania 26)
Bret Hart is a technical mastermind and someone who puts together amazing matches consistently. However, post-concussion syndrome and a stroke severely impacted the Hitman’s overall health, and by the time he competed against Vince McMahon, he wasn’t the same person.
While it was brilliant seeing him back involved in professional wrestling, Hart could no longer work at the same level and a lengthy match against Vince McMahon likely wasn’t the best way to highlight him.
2 Kurt Angle (Vs. Baron Corbin – WrestleMania 35)
Kurt Angle is one of the best in-ring talents of all time, being someone who brought incredible intensity every time he stepped into the ring. However, his final run in WWE saw him put together some forgettable performances that showed his body had certainly slowed down a lot.
The most memorable match in that run took place at the end against Baron Corbin because it was his final ever encounter. However, even then Angle couldn’t muster up a great performance as he struggled to get through their brief match that didn’t end his career in the way people hoped.
1 The Undertaker (Vs. Roman Reigns – WrestleMania 33)
The Undertaker is one of the most iconic wrestlers of all time, and he is someone who deserved the perfect send-off due to how long he spent in the business. However, the Deadman arguably stuck around too long searching for that perfect match, and it led to some poor performances taking place toward the end of his career.
Unfortunately for him, one of those just so happened to be in the main event of WrestleMania 33. In what could have, and should have been the ideal goodbye, he struggled to get through the match with Roman Reigns. Undertaker knew his performance wasn’t good enough, which is something he has openly spoken about, even apologizing to Reigns for it.