On a cold winter day in Hamilton, Ontario on January 24, 1988, the WWE began a wrestling tradition that has stood the test of time and has become one of the promotion's major annual events. All the greatest wrestlers of the past several decades have made their way to the ring to participate in this epic event. Legends have been made and champions have been crowned.

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The luck of the draw can contribute much to success, but in the event's history, there have been multiple wrestlers that have bucked the odds of an early entrance into the Royal Rumble to post improbable runs. Here are the ten longest amounts of time an individual competitor has spent in a single Royal Rumble.

UPDATE: 2022/01/19 12:00 EST BY TEVON KING

The Royal Rumble is all about the numbers, and there are a plethora of records that have been broken over the years at the Royal Rumble. Of course, the main aim of entering a Royal Rumble match is to win, but not every wrestler is fortunate to book their spot in a World Championship match at WrestleMania. Some wrestlers have built a reputation for being the "Iron Man" in Royal Rumble matches by surviving a long time in a Royal Rumble match. Rumbles are enticing but energy-sapping matches. However, whilst it may be impressive with some wrestlers reaching the latter stages of a Royal Rumble, some have spent more time outside the squared circle than in it. Ultimately, the wrestlers with plenty of endurance generally do well in Royal Rumble matches.

UPDATE: 2023/01/23 14:00 EST BY TEVON KING

The Royal Rumble match is one of the most hotly anticipated matches that wrestling fans can't wait to watch. The prize for winners of the men's and women's Royal Rumble matches is a World Championship match at WrestleMania. However, the Royal Rumble match is all about endurance, the earlier you enter the Royal Rumble match. The "Iron Man" or "Iron Woman" in a Royal Rumble match is the person who spends the longest amount of time in Royal Rumble matches. Whilst, there are no prizes handed out for wrestlers that spent a long time in the Royal Rumble match, it is still a good achievement to last in a Royal Rumble match for a long time.

18 Ember Moon - 52:23 (2019)

Ember Moon entered the 2019 women's Royal Rumble match as the sixth entrant, and she wasn't a contender to go all the way to win the match. However, Moon endured 52 minutes and 23 seconds in the Royal Rumble which is a valiant effort.

What's interesting about the former NXT Women's Champion's performance is that she failed to register a single elimination during her stint in the Rumble. Moon's performance isn't memorable by any stretch, and she was eliminated from the match by Alexa Bliss.

17 Kane - 53:46 (2001)

Business picked up when Kane entered the 2001 Royal Rumble match as the sixth participant. The Big Red Machine set a record of 11 eliminations, which stood for 13 years, and he was in good shape to win his first Royal Rumble match.

Kane managed to reach the final two, but it took several chair shots and a clothesline from Steve Austin for the Texas Rattlesnake to win his third Royal Rumble match in five years. Kane lasted almost 54 minutes, and it was a superb outing for the former WWE Champion, especially when he linked up with The Undertaker to remove multiple wrestlers from the equation.

16 Sasha Banks - 54:46 (2018)

Of course, none other than "The Boss" Sasha Banks would become the first number-one entrant in the first women's Royal Rumble match in 2018. There's no surprise that the newly named Mercedes Mone set the pace by producing a fantastic performance that was worthy of winning the women's Royal Rumble match.

The Boss banked 54 minutes and 46 seconds, and she eliminated Trish Stratus and Bayley from the titular bout. She even assisted several other competitors in getting rid of Vickie Guerrero from the match. Ultimately, Banks failed to go all the way as The Bella Twins eliminated her.

15 Natalya - 56:01 (2019)

Natalya is one of the most underrated female wrestlers who doesn't get the credit she deserves. The former SmackDown Women's Champion entered the second annual women's Royal Rumble match in 2019 as the second entrant.

She was hoping to follow in the footsteps of her uncle Bret Hart who won the Royal Rumble match alongside Lex Luger in 1994. Unfortunately for her, Natalya only eliminated Liv Morgan and Sarah Logan from the Royal Rumble match. However, it was a respectable performance as she lasted 56 minutes and one second before Nia Jax brought a halt to her participation in the Rumble.

14 Steve Austin - 56:38 (1999)

The 1999 Royal Rumble match was massively underwhelming since it was exclusively centered around Steve Austin and Mr. McMahon. The Texas Rattlesnake entered the Royal Rumble match from the unenviable number one position, and he was aiming to become the first man to win three Rumble matches in succession.

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Austin and McMahon spent a large portion of the Rumble away from the ring. However, once Austin returned to the arena after going to the hospital, he eliminated eight competitors with ease. Austin should have won the 1999 Royal Rumble match, but he didn't with Mr. McMahon tossing him over the top rope, all thanks to the new WWE Champion The Rock.

13 Mr. McMahon - 56:38 (1999)

Mr. McMahon spent very little time for one of the longest times ever in a Royal Rumble in the ring. As the second entrant announced, Mr. McMahon's greatest fears were realized when he was forced into the ring alone with Stone Cold Steve Austin. He most likely would have been eliminated quickly if more competitors had not entered, coupled with McMahon fleeing. He was followed by Austin, who was attacked by members of The Corporation. Mr. McMahon returned to the ring and spent most of his time in the broadcast booth. Despite his early injuries, Austin returned, cleared the ring, and forced Mr. McMahon back into action as they were the last two competitors. Interference by The Rock gave McMahon the window he needed, as he was able to eliminate the distracted Austin to claim victory.

12 Bianca Belair - 56:52 (2021)

Bianca Belair was the MVP of the women's Royal Rumble match for two consecutive years in 2020 and 2021. However, the EST of WWE's outing in the 2021 women's Royal Rumble match was nothing short of extraordinary.

Belair entered third, and she was the final woman standing with a convincing performance. Belair eliminated Bayley, Natalya, Charlotte Flair, and Rhea Ripley on her way to winning the Royal Rumble match. She has set the record for the longest time spent for a woman in a Royal Rumble match by clocking 56 minutes and 52 seconds under her belt.

11 Finn Balor - 57:38 (2018)

One of the original two entrants in the 2018 edition of the Royal Rumble, Finn Balor's efforts were monumental as he made it to the final four competitors after he eliminated Rey Mysterio.

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Ending the night for four total participants (tied for the most in this particular Royal Rumble), Balor ran out of gas as he eventually was a victim of John Cena, spending nearly an hour in the ring to ultimately come up empty-handed.

10 Randy Orton - 58:30 (2021)

Randy Orton started the 2021 men's Royal Rumble match as the second entrant alongside his former tag team partner Edge. The Viper lasting 58 minutes and 30 seconds sound impressive, but it couldn't be further from the truth.

Orton did the bare minimum in this Rumble match as the Rated-R Superstar targeted Orton's leg with a couple of steel chair shots. That ruled Orton out of the equation until he tried to secure a third Rumble victory by planting Edge with an RKO. Edge outsmarted him and tossed Orton over the top rope to win the Rumble once more.

9 Edge - 58:30 (2021)

Unfortunately, no fans were physically present to witness Edge's second Royal Rumble victory in 2021 because of the COVID-19 pandemic. The WWE Hall of Famer entered the Rumble drew the unfavorable number one position, but he managed to last the course.

Edge made a shocking return to the Rumble in 2020 but 2021 was all about winning it. Just like the 1995 Royal Rumble match, the first two participants occupied the final two positions. 11 years to the day after his first Rumble triumph, Edge punched his ticket to WrestleMania once again after lasting two minutes shy of an hour.

8 Ric Flair - 59:26 (1992)

Many consider Flair's win in 1992 to be the best performance ever in Royal Rumble history. As the third entrant, Flair fought tooth and nail for this rumble's ultimate prize, the vacant WWE Championship. Many of the greatest wrestlers of the time took part due to the high stakes (this was the first time the title or title shot was attached to a victory), but Flair's fortitude throughout eventually led him to a showdown with Sid Justice.

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With a little help from a distraction by Hulk Hogan, the emotionally and physically spent Flair mustered up the courage and strength to end Sid Justice's night and claim his first WWE Championship, further cementing his legacy.

7 Roman Reigns - 59:48 (2016)

Coming in as entrant #1, Roman Reigns spent 12 seconds short of an hour in the ring fighting to retain his WWE Championship. This was a stipulation that was made part of the event by an enraged Vince McMahon, who was disgusted with Reigns' continued disrespect of his family.

Despite earlier attempts, McMahon got what he wanted in the loss of the title, as Roman Reign's colossal efforts came up short. Making it to the final three, Triple H (who was entrant #30) eliminated him and went on to win the Royal Rumble and take home the WWE Championship. Reigns was able to exact revenge and regain the title at WrestleMania later that year.

6 Chris Jericho - 60:13 (2017)

The 2017 Royal Rumble almost saw one of the two original participants run the table and win, as Chris Jericho (entrant #2) spent over an hour in his quest to gain a world championship shot at WrestleMania 33. His efforts that night did put his career total in the Royal Rumble around five hours (a record), and he would make it to the final four before a fresh Roman Reigns ended his night.

5 Triple H - 60:16 (2006)

Triple H strode to the ring as entrant #1 in 2006 and began this epic event with another that landed in the top ten longest times in a Royal Rumble, Rey Mysterio. Triple H had a great night as he eliminated six participants (including big names Ric Flair, Kane, and The Big Show) on his way to the final three.

The victory was not to be his that night and there was no world championship match this time for Triple H. We can't feel too bad for him though, as his career fourteen world championship reigns more than makes up for the disappointment of not being able to finish off his epic performance that night.

4 Bob Backlund - 61:10 (1993)

Bob Backlund held the record for the longest time as a competitor in a single Royal Rumble for over a decade with his monumental effort in 1993. Finishing third, Backlund, who spent eight years out of the WWE in the mid to late 80s to early 90s, used his work that night to rejuvenate his career. This rejuvenation culminated the next year as Backlund defeated Bret "The Hitman" Hart for the WWE Championship in a "Throw In The Towel" submission match (albeit with some assistance from Owen Hart). This allowed Bob to set a different record... the longest time between WWE Championship reigns. Backlund took home the title just short of eleven years after he lost it to the Iron Sheik. Not too bad for a wrestler that began his amateur wrestling career at tiny Waldorf College in Forest City, Iowa.

3 Chris Benoit - 61:31 (2004)

Even though the WWE would like to forget its history with Chris Benoit, there is no hiding from the work the "Canadian Crippler" did at the Wachovia Center in Philadelphia in 2004. As an entrant in the Royal Rumble that year, Benoit broke the over-decade-old record of total time as a participant in a single rumble, and he was also only the second winner to that point to enter at #1.

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The mammoth win allowed Benoit to compete for and win his only World Heavyweight Championship later in the year at WrestleMania 20, as he defeated Triple H and Shawn Michaels in a triple threat match.

2 Rey Mysterio - 62:12 (2006)

Billed at 5'6 and 175 lbs., Rey Mysterio stood taller than any of the giants of the WWE during the Royal Rumble of 2006. Withstanding physical assaults successfully for over an hour, the underdog found himself in the unenviable position of facing former Evolution members Triple H and Randy Orton as part of the final three.

Eliminating both, Rey Mysterio finally broke through to the upper echelon of the WWE with the win, and eventually solidified his place there when he won the World Heavyweight Championship over Randy Orton and Kurt Angle at WrestleMania 22. One of the most exciting wrestlers ever, Rey Mysterio would never need to return to a mid-carder status.

1 Daniel Bryan - 76:05 (2018 Greatest Royal Rumble)

WWE recognizes Daniel Bryan as the record holder for the longest time spent in a single Royal Rumble. Although his efforts were phenomenal, the legitimacy of this record is certainly a point of contention for many wrestling fans. The 2018 Greatest Royal Rumble had a record 50 participants, in comparison with a typical Royal Rumble only allowing 30. Nevertheless, Bryan put in a long night's worth of work to just get to the final three. Ultimately coming up short, it seemed as if no one was going to deny Braun Strowman on that evening, as he eliminated a whopping thirteen competitors on the way to his win. Ironically enough, Daniel Bryan was not one of those thirteen.