An Iron Man match is a rarely used stipulation used in WWE. The promotion's penchant for booking matches that usually last between 10 and 20 minutes, even on pay-per-view, does not lend itself well to the time-consuming nature of an Iron Man match.
However, over the years, the stipulation has been used to varying degrees of effect. It has been used as a tool in championship feuds, usually to end them. While there have been some 15-minute sprints dubbed as 'Iron Man' matches, 30-minute or 1-hour ones are most commonly associated with the stipulation. This will not include matches at live events and dark shows, or 15-minute Iron Man matches.
9 Triple H Vs. The Rock (Judgment Day, 2000)
Triple H and The Rock were in the main event Judgment Day in 2000. The Iron Man Match for the WWF Championship was refereed by Shawn Michaels and started off well enough.
With the match tied at 5-5 and just a few minutes to go, DX and the McMahon Family all got involved, causing Michaels to get knocked out in the process. The Undertaker returned and dropped Triple H with a Tombstone Piledriver as Michaels surfaced. The Rock lost the fall via disqualification and the WWF Championship was awarded to The Game. It was a terrible, convoluted way to win a major championship that ended up souring fans on the whole experience.
8 Dolph Ziggler Vs. Seth Rollins (Extreme Rules, 2018)
In the main event of Extreme Rules in 2018, Dolph Ziggler defended his Intercontinental Championship against Seth Rollins in a 30-minute Iron Man match. The pacing of this match was completely off, as Rollins picked up a 3-0 lead less than halfway into the match.
The arrival of Drew McIntyre, who came to help out Ziggler, evened things up for The Showoff. After taking the lead, the momentum of the match ground to a halt, as Ziggler worked over Rollins with a number of holds. Rollins dropped Ziggler with a sunset flip to even up the score at 4-4 as the clock ran out. Kurt Angle sent the match into sudden-death overtime; McIntyre distracted Rollins, allowing Ziggler to pick up the win in seconds. The underwhelming finish, paired with poor pacing left the fans feeling dissatisfied.
7 Brock Lesnar Vs. Kurt Angle (Smackdown, 2003)
Brock Lesnar and Kurt Angle waged war once more for the WWE Championship on an episode of Smackdown in 2003. The epic 1-hour Iron Man match unfortunately failed to live up to the lofty expectations fans had, especially after their WrestleMania XIX masterpiece.
Poorly-placed ad breaks meant that viewers at home also missed out on spots, including Lesnar dropping Angle with a massive Superplex. Lesnar emerged victorious 5-4 and won the WWE Championship in a match that was certainly above average but crumbled under the weight of its own expectations.
6 The Bar Vs. The Hardy Boyz (Great Balls Of Fire)
Regardless of the questionable name given to the pay-per-view, Great Balls of Fire had a card stacked with great matches. Midway through the night, The Bar defended the Raw Tag Team Championships in a 30-minute Iron Man match against The Hardy Boyz.
With Sheamus picking up a pinfall in the first five seconds, the faces were on the back-foot almost immediately. The heels then quickly made it 3-0 in their favor before the faces surged back to even things up. In the dying moments of the match, Cesaro pinned Jeff to make it 4-3 and ran out the clock. It was a fun match that made good use of the stipulation, but the relatively low stakes made it hard to get invested in the match.
5 Chris Benoit Vs. Triple H (Raw, 2004)
After a historic win at WrestleMania XX, Chris Benoit rolled into the biggest challenge of his career in a 1-hour Iron Man Match for the World Heavyweight Championship. Triple H picked up a 3-1 lead and threatened to bring a premature end to Benoit's fairy-tale run.
But Benoit overcame the deficit, an injured back, and interference from Batista and Ric Flair to beat The Game and retain his championship. It was a strong match that allowed Triple H to work a more technical match, but it was let down by it not being on a pay-per-view and the mildly predictable outcome.
4 John Cena Vs. Randy Orton (Bragging Rights, 2009)
John Cena took on Randy Orton in an Anything Goes 1-Hour Iron Man Match in the hopes of beating The Viper for the WWE Championship. The 'Anything Goes' addition allowed both men to work a hardcore match that included setting off pyro and The Viper doing everything possible to keep Cena down.
The creative use of weapons and both men digging deep into their move-set greatly elevated the match. Cena picked up the win by tapping out Orton to the STF in the last few seconds of the match to successfully win the WWE Championship. The high stakes and weapon-use were big positives, but in the era of Super Cena, it still felt a little predictable.
3 Charlotte Flair Vs. Sasha Banks (Roadblock: End Of The Line)
Raw Women's Champion Sasha Banks and Charlotte Flair continued their battle for the Raw Women's Championship with a 30-minute Iron Man match. After a slow start, with both women feeling each other out, the pace picked up considerably.
With Banks leading 2-1, Flair began targeting Banks' knee and continued to wear down The Boss. Despite her best efforts, Banks tapped out to make it 2-2 as the clock ran out. In sudden-death overtime, Flair trapped Banks in the Figure Eight once more and picked up the win, getting back the championship she had lost just days earlier. The timing of the falls and the match psychology, combined with the unexpected finish elevated the quality of the match.
2 Shawn Michaels Vs. Bret Hart (WrestleMania XII)
WWE billed this match as the promotion's first Iron Man match, and in a sense, it was, as all the previous matches had taken place at live events and dark shows. In the main event of WrestleMania XII, the veteran Bret Hart took the fight to the younger, hungrier Shawn Michaels.
The first 40 minutes of the match mainly had them wearing each other down, while the pacing hit a fever pitch in the last 20 minutes as both men desperately tried to get the pinfall that would win the match. With the score tied at 0-0 after 1-hour, the match headed into sudden-death overtime, where Michaels finally managed to pick up the win and the WWF World Heavyweight Championship in one of the biggest matches of his career.
1 Bayley Vs. Sasha Banks (NXT TakeOver: Respect)
For the first time in TakeOver history, the event had women work the main event. Bayley defended her NXT Women's Championship against Sasha Banks in a 30-minute Iron Man Match. The match was the perfect display of Banks' cunning and Bayley's heart. With the score tied at 2-2, Banks trapped Bayley in the Banks Statement, but somehow, Bayley was able to shift her weight and trap Banks in an armbar of her own. Combined with kicks to the head, Banks had no choice but to tap, as Bayley successfully defended her championship in a phenomenal match.
After the match, Triple H and William Regal headed to the ring and presented them with flowers, as the rest of the roster applauded them from the entrance trap. It was a game-changing effort from both women, who put on a fantastic match full of great character work, thrilling sequences, and a great finish.