At one time, people looked to the WrestleMania XII match between Shawn Michaels and Bret "The Hitman" Hart as the most significant Iron Man match in wrestling history. However, things didn't start or end with that match, as Iron Man matches in WWE have created some of the company's greatest moments.
Over the years, the Iron Man matches have changed, with the 60-minute time limit dropping to 30 minutes in recent years. Even AEW had an Iron Man match recently, with Kenny Omega beating PAC in overtime. In WWE, there are plenty of fantastic options when looking for an Iron Man match, and here are the 10 best in WWE history, ranked.
10 SETH ROLLINS VS. DOLPH ZIGGLER
Dolph Ziggler and Seth Rollins fought in a 30-minute Iron Man at the Extreme Rules in 2018 for the Intercontinental Championship. The match was great, but there was one thing holding it down. The fans in attendance in Pittsburgh didn't seem to care.
However, despite the fans delivering dueling chants and not doing their part, the two told a great story with the heel Ziggler doing everything he could to beat Rollins. They went 4-4 in the 30 minutes, and then Kurt Angles demanded overtime, where Drew McIntyre distracted Rollins so Ziggler could earn the cheating victory.
9 CHARLOTTE FLAIR VS. SASHA BANKS
At the Roadblock: End of the Line PPV event in 2016, the women turned in a clinic in an Iron Man match. Much like they had since the Women's Evolution started, Sasha Banks and Charlotte Flair led the way as the two women who broke barriers and battled each other in matches generally saved for the men.
In this Iron Man match, it was a 30-minute time limit with the Raw Women's Championship on the line. Charlotte went up 1-0, and then Banks got a pin and a submission to go up 2-1. Charlotte then made Sasha tap with five seconds left to tie it up. In overtime, Charlotte made Sasha tap again to win.
8 HARDY BOYZ VS. THE BAR
At Great Balls of Fire in 2017, an unusual match took place as two tag teams battled in an Iron Man match. This saw Raw Tag Team Champions, The Bar (Cesaro and Sheamus) defend their titles against the Hardy Boyz in a 30-minute Iron Man match.
The match saw The Bar take a 2-0 lead before The Hardy Boyz finally scored their first pinfall. The Bar went up 3-1, and then the Hardy Boyz rallied to tie it at 3-3. There would be no overtime, though, as The Bar scored their fourth fall in regulation, and time ran out before the Hardys could come back one more time.
7 CHRIS BENOIT VS. TRIPLE H
Not all Iron Man matches take place at pay-per-view events. In 2004, Triple H and Chris Benoit wrestled a one-hour Iron Man match on an episode of Monday Night Raw. Remember, Benoit had proven to be a surprise star, beating Triple H and Shawn Michaels in a triple threat to win the world title.
One thing that makes this match special is that Chris Benoit was always able to bring out the best in Triple H from an actual wrestling standpoint. Despite interference by members of Evolution, Benoit was able to come back and beat Triple H from a 3-1 deficit to keep his title.
6 JOHN CENA VS. RANDY ORTON
Randy Orton and John Cena had one of the longest-lasting feuds of any WWE superstars. They came up from developmental at the same time in 2002, and both men became multi-time world champions. Cena was the ultimate babyface, and Orton was one of the meanest heels in history.
At Bragging Rights in 2009, John Cena and Randy Orton fought in an Iron Man match that was also a no disqualification/anything goes match, something unique at the time. Cena busted his head open, the two men hit each other with everything, and Cena still came out the winner.
5 CHRIS BENOIT VS. KURT ANGLE
Chris Benoit is on here twice and for a good reason. He was one of the best technical wrestlers on the planet, and that was important in long matches, such as an Iron Man match. When he battled Kurt Angle, the two put on some of the best technical wrestling matches in WWE history.
This Iron Man match took place at Backlash in 2001, and the twist here is that it was also a submissions-only match. For 30 minutes, the two used every submission move imaginable. The match went into overtime, and Benoit won with his Crossface.
4 TRIPLE H VS. THE ROCK
Triple H's second match on this list came in 2000 during his long-running feud with The Rock. This feud took place while Stone Cold Steve Austin was out of action following neck surgery, and they both moved to the top of WWE, feuding for the world title.
This was at Judgment Day, was only the second Iron Man match in WWE history, had a 60-minute time limit, and featured Shawn Michaels as the referee. After 58 minutes, they sat tied, 5-5. The ending was a screw job with Undertaker attacking Triple H, resulting in him winning by DQ, 6-5. However, what came before was perfection.
3 BROCK LESNAR VS. KURT ANGLE
Kurt Angle's second match on this list was against Brock Lesnar. While people give Lesnar crap now for only wrestling limited dates and almost always short matches, he proved here that he could go the limit and look like a million bucks doing so. This was also a televised match.
The two men fought in an Iron Man match on SmackDown in September 2003. The only thing holding it down somewhat was the commercial breaks, but that did not stop them from bringing down the house. The match ended with Lesnar up 5-4 while locked in Angle's ankle lock as time expired.
2 SASHA BANKS VS. BAYLEY
The second best Iron Man match in WWE history took place in NXT. The match was part of TakeOver: Respect in 2015 and featured Bayley defending her NXT Women's Title against Sasha Banks in a 30-minute Iron Man match.
This was another chance for Bayley to prove that she was the top woman in the game. The two fought hard, as they always do against each other, and it was a smart story. With 13 minutes left, they were tied 2-2, and neither woman would give in. Finally, Bayley locked in a modified armbar, and Sasha tapped out, without realizing she only had seconds left to reach the time limit.
1 BRET HART VS. SHAWN MICHAELS
It is hard to say anything bad about Shawn Michaels vs. Bret Hart at WrestleMania XII, the match that introduced fans to the entire idea of an Iron Man match. The story was brilliant. Hart was the cocky and brash babyface who hated everything Michaels stood for. Michaels was fighting to achieve his childhood dream of one day winning a world championship.
It was a 60-minute Iron Man match. There was also one thing unique about this, as the two men took each other to the limit, and neither gained a pinfall or submission in the allotted 60 minutes. Finally, they went into overtime, and Michaels achieved his dream and won the first world title of his career in just over one hour of action.