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Wrestlers Who Won The Royal Rumble Match Twice (And Won Who Won Three Times!)

Wrestlers Who Won The Royal Rumble Match Twice (And Won Who Won Three Times!)

The Royal Rumble is the most highly anticipated event in the wrestling calendar. It features the most fun and exciting match type in wrestling, the Royal Rumble match. It’s a thirty man over the top rope Battle Royale, with staggered entrances every 90 seconds.

This allows WWE to introduce surprise entrances, and to have the crowd kept engaged for over an hour as the match goes on. It also is a great place for wrestlers to return, whether from injury, as new signings or as returning legends looking for one last hurrah.

In the 34 years since the event began, the winner of the Royal Rumble has been one of the most prestigious prizes in wrestling. The winner earns themselves a title match in the main event of Wrestlemania, although some years the match itself has been for the WWE Championship (1992 & 2016)

Ric Flair won the 1992 Royal Rumble
Ric Flair won the 1992 Royal Rumble to become WWE Champion

Out of all the winners of the match, only 9 men have won the Royal Rumble multiple times. To win it once is an impressive feat, to win it twice is incredible. To win it for a third time, that makes you an all time great and a legend of the sport.

Here are the eight wrestlers who won the Royal Rumble match twice, and won who managed an astounding three Royal Rumble victories.

Hulk Hogan – 1990 & 1991

Hulk Hogan is one of the greatest WWE superstars of all time. It is not surprise that he was the first person to win the Royal Rumble match multiple times.

His first victory came in the 1990 Royal Rumble, which was slightly different to modern times. Back in those days, the winner of the Royal Rumble match didn’t earn themselves a Wrestlemania championship match by winning.

They simply won the great feeling you get by winning a wrestling match. And as the reigning WWE Champion, Hulk Hogan would have gained nothing for winning a Wrestlemania title match.

He had a great performance in the 1990 Royal Rumble. Hogan eliminated 6 men, including the runner up Mr Perfect to win the match and etch his name in history once again.

Hogan won his second Royal Rumble the year later, becoming the first person to not just win two of the matches, but to win them consecutively. The year running up to the match, Hulk Hogan had been feuding with the monstrous Earthquake. Hogan beat the giant at every turn, making it a rather one-sided affair.

This feud ended once and for all when Hogan eliminated Earthquake, as well as six other men, to win the 1991 Royal Rumble. He would go on to beat Sgt Slaughter at Wrestlemania VII to win the WWE Championship, which he lost the Wrestlemania prior against Ultimate Warrior.

Shawn Michaels – 1995 & 1996

The Heart Break Kid became the second man to win two Royal Rumble matches in a row. As one of the greatest in-ring talents of all time, fans of Shawn Michaels couldn’t way to see him battle his way to the top of WWE by winning one of the most gruelling matches of all.

Michaels had the honour of being the first man to enter the Royal Rumble at number 1 and last all the way to the end. In 1995 he drew the dreaded first spot, but his incredible stamina and wrestling technique meant that he could hold on right to the very end.

Holding on is also exactly what he did. At the matches climax, British Bulldog threw the American star over the top rope and heard his foot hit the floor. He went off the celebrate, but the camera’s caught Michaels clinging onto the ropes for dear life as one of his feet grazed the floor below.

With the rules requiring both feet to hit the floor, Shawn Michaels clambered back into the ring and knocked the celebrating British Bulldog off the top rope, winning the Royal Rumble in extraordinary fashion.

Not content with just one history making performance, Shawn Michaels won the Royal Rumble match again, a year later at the 1996 Royal Rumble.

This time the field was a little easier for the Heart Break Kid. The Hall of Famer drew the number 18 slot, a lifetime away from his number 1 entry the year prior. Despite his relatively late entry, he still managed to rack up an impressive 8 eliminations on his way to second consecutive Royal Rumble win.

He would use his hard earned title shot to take on Bret “The Hitman” Hart at Wrestlemania XII. He defeated his fierce rival at the event, winning in overtime as the pair drew inside 60 minutes during their legendary Iron Man match. Michaels won the WWE Championship and achieved his famous “Boyhood Dream”.

Steve Austin – 1997, 1998 & 2001

No man can claim to be more successful in the Royal Rumble than Stone Cold Steve Austin. The WWE Hall of Famer is the only man to have won not one, not two but three Royal Rumbles.

It just goes further to prove that Steve Austin is one of the greatest WWE wrestlers of all time and the most popular wrestler since Hulk Hogan dominated the scene in the 1980s.

His first win was in 1997 and came in controversial fashion. The Rattlesnake eliminated ten men, a record at the time, before being unceremoniously dumped out of the match by long-term rival Bret Hart.

However thanks to a ringside brawl between Mankind and Terry Funk, referees missed Austin’s feet hit the ground as he snuck back into the match won the match. He eliminated massive stars including Undertaker, Vader and Bret Hart en route to victory and showed the Stone Cold Steve Austin was the top man in WWE.

Not content with just one victory, the next year Austin doubled his win tally. However this time there was no controversy, as Austin was nearing his peak of popularity. He outlasted 29 other men for the second time in a row in 1998 to win the Royal Rumble match and earn his shot at Shawn Michaels at Wrestlemania XIV.

The Texas Rattlesnake last eliminated his greatest rival – The Rock – last before winning the Royal Rumble match. He became the second man to win the match twice, but no-one had ever won it thrice.

Austin was the first and only man to win three Royal Rumble matches. His third came 3 years after his second, with a runner up position behind winner Vince McMahon coming in 1999. It took until 2001, now at the peak of his popularity, for Austin to win his third Royal Rumble match.

He eliminated Kane last to win the match. Kane eliminated a record 11 men in that match but could not withstand the force of the Bionic Redneck. Austin won the match and went on to face The Rock in one of their three huge Wrestlemania matches to win the WWE Championship.

Triple H – 2002 & 2016

While some fans deny Triple H’s crown as a main event star, their is no doubting that he is one of the most successful WWE superstars in the history of the business. Even to this day people clamour for a Triple H return to the ring.

The exact same thing happened in 2002. During a match where he tagged with Stone Cold Steve Austin against the team of Chris Jericho and Chris Benoit, Triple H suffered a brutal injury that could have been career threatening. He tore his quadricep completely off the bone and missed eight months of in-ring action, with some fearing he would never wrestle again.

However, the building exploded when the Game returned to WWE after eight months out, on Monday Night Raw. Decked out in the most ridiculous denim-on-leather-on-denim outfit you’ll ever see, he returned in front of the baying Madison Square Garden crowd to official announce his return and subsequent appearance in the 2002 Royal Rumble.

Triple H went on to win the 2002 Royal Rumble by last elimination Kurt Angle. He used his title shot to take on Chris Jericho in the main event of Wrestlemania X8, where he won the WWE Undisputed Championship.

However, it is known as one of the least memorable Wrestlemania main events. The match had to follow the legendary Rock vs Hulk Hogan match, and never stood a chance getting the crowd invested after watching such a brilliant, emotional match.

It would take another 14 years before he would taste Royal Rumble victory. Despite coming close in 2006, 2008 and 2009, it was his big return in 2016 that would be his second and last Royal Rumble win.

The Authority were sick of Roman Reigns as champion, joining the rest of the WWE fans who wanted anyone but Roman Reigns as the main eventer on Raw. They forced Roman to put his WWE Championship on the line inside the Royal Rumble, with the Big Dog having to outlast 29 other men to keep hold of his WWE title.

It was all going well for the Big Dog, who entered the match from the number one. Unfortunately, Triple H returned for the first time in months, after an attack from Roman Reigns, to enter the match at number 30. He eliminated Reigns and his former partner Dean Ambrose on route to become the Royal Rumble winner and WWE Champion.

He lost the belt in a unmemorable match at Wrestlemania 33 to Reigns, although he did have a fantastic title defence against Dean Ambrose (Jon Moxley) at WWE Roadblock just prior to Wrestlemania.

Brock Lesnar – 2003 & 2022

The most recent man to join the “Multiple Royal Rumble Winners Club” is the Beast Incarnate himself, Brock Lesnar.

The former “Next Big Thing” and current “Big Thing” won his debut Royal Rumble match in 2003, less than a year after debuting on the main roster.

It was a meteoric rise never seen before or since, and the Next Big Thing last eliminated The Undertaker to win the Royal Rumble match at the first time of asking.

He went on to win the WWE Championship at Wrestlemania XIX, where he defeated the Olympic Gold Medallist Kurt Angle in a breathe taking main event. However, the match is infamous for Lesnar attempted a shooting star press toward the end of the match, but messing up and landing on his head and breaking his neck.

Lesnar next won the Royal Rumble in controversial circumstance. The 2022 Royal Rumble had been a dull affair, with weak star power and strange pacing that failed to engage the audience begging for a hero to cheer.

With 29 entrants already in the match, fans were expecting something big for number 30. Sadly, Lesnar entered the match, hours after he lost to WWE Championship to Bobby Lashley earlier in the night thanks to interference by Roman Reigns.

WWE had made it clear that Roman Reigns vs Brock Lesnar was the main event for Wrestlemania 38, and fans were just hoping that the build for the unwanted match would be at least slightly interesting.

Sadly, it was not. Lesnar lasted only 2 and half minutes as he tossed out everyone left on the field and won his second Royal Rumble match. This set up a Wrestlemania Main Event at Wrestlemania 38, and the big Royal Rumble win earned WWE plenty of bad press with their unimaginative and damaging winner.

Batista – 2005 & 2014

Both of Batista’s Royal Rumble wins were met with very different reactions. He has won the Royal Rumble match twice, but with polar opposite reactions each time.

In 2005 he overcame the odds to beat 29 other men to win the Royal Rumble. It led to one of the great feuds in WWE history, as he used his title shot to turn on Triple H and beat him for the World Heavyweight Championship at Wrestlemania 22.

That Rumble was famous for a freak occurrence happening at the end. By mistake, both John Cena and Batista fell out the ring at the same time, with video replays showing that their feet hit the floor at exactly the same time.

This was followed by Vince McMahon storming down the ring, demanding the match to restart. In his fury, he tore both his quads and sat in the ring barking orders in the funniest way possible.

The match was restarted and Batista threw Cena out of the ring, and earned his shot at The Game at Wrestlemania.

Batista’s second Royal Rumble victory was met with much less applause, and more burning hatred.

He announced his return, which had leaked online, the week prior to the Royal Rumble, and told the world he was going to win the match and the WWE World Heavyweight Championship at Wrestlemania.

Any other year and the fans would be on board and singing along with his incredible theme song. However fans were so into Daniel Bryan that they booed anyone that wasn’t The Dazzler. This included Batista, who’s return after four years was ruined and forced a heel turn upon him due to Daniel Bryan’s overwhelming popularity with the fans.

The 2014 Royal Rumble which Batista won was voted one of the worst Royal Rumble matches ever.

John Cena 2008 & 2013

Despite being a polarizing figure, John Cena’s Royal Rumble are usually remembered as being great moments in WWE. John Cena has won the Royal Rumble match twice, joining an elusive club when he picked up his second victory in 2013.

The 16-time WWE Champion is one of the most decorated WWE stars in history, but it took him a while from his debut to finally win one of the biggest matches in WWE.

Cena came as runner up to Batista in the 2005 Royal Rumble, but managed to do one better in 2008. After months out of the ring with injury, he shocked fans by returning half a year early as a shock number 30 entrant in the Royal Rumble.

After a stare down with rival Triple H, John Cena cleared house and eventually tossed out The Game to win the 2008 Royal Rumble in Madison Square Garden. Sadly he would fail to capitalise on this victory, losing to Randy Orton at No Way Out and Wrestlemania that year in WWE Championship matches.

Cena added to his portfolio of Royal Rumble wins when he entered the 2013 WWE Royal Rumble. Locked in a rivalry with The Rock, he needed to win the match in order to face off with him at Wrestlemania for the second consecutive year.

On the same night that John Cena last eliminated Ryback to win the 2013 Royal Rumble, The Rock ended CM Punk’s legendary 434 WWE Championship reign to win his last WWE Championship. This set up the twice in a lifetime match between John Cena and The Rock, for the main event of Wrestlemania 29.

Unlike the previous year in Miami, John Cena beat The Rock in the most successful Wrestlemania of all time. A record number of fans saw Cena pin The Rock and reclaim the WWE Championship that he had not held for nearly two years.

Randy Orton – 2009 & 2017

Randy Orton was the fourth member of Evolution to win the Royal Rumble match and the third of them to win two Royal Rumble matches.

Orton had been a star in WWE for years, and a former World Champion, when he finally won the Royal Rumble match in 2009. With the help of his Legacy team mates (Cody Rhodes & Ted DiBiase Jr) he outlasted 30 other men, last eliminating former friend Triple H, to win the Royal Rumble match.

It came as no surprise as Orton was the long time favourite for the match after his incredible run as the top heel in WWE as the psychopathic “Viper”. He went on to face Triple H in the Wrestlemania main event, in a match that disappointed, partially due to them going on after the classic Shawn Michaels vs Undertaker match.

His second Royal Rumble win was a huge surprise. He had been indoctrinated into the Wyatt Family by Bray Wyatt, and with Wyatt’s help threw Roman Reigns out of the Rumble and won the match.

Orton would defeat Wyatt for the WWE Championship at that years Wrestlemania. Wyatt beat John Cena and four other men inside the Elimination Chamber, before Orton turned on him at the culmination of the year long storyline between the pair.

Edge – 2010 & 2021

Edge has one notable thing about his Royal Rumble wins that the other eight men cannot claim. Both times he won the match he was returning from injury, and was not expected to win the match at all.

The Rated-R Superstar was just getting his groove in his tag team with Chris Jericho, but then a recurring neck injury struck. The Canadian superstar was on the side-lines for nearly a year and was expected to miss not only the Royal Rumble, but Wrestlemania too.

Fans were shocked when the buzzer rang and Edge entered the Royal Rumble. His entrance was a complete surprise, and was entering an already star studded field. He joined John Cena, Chris Jericho, Batista and Shawn Michaels in the final five of the Royal Rumble match.

Somehow he outlasted them all and punched his ticket to Wrestlemania with his Rumble win. However, just like many others on the list, he failed to win his Wrestlemania match and win the World Heavyweight Championship from Chris Jericho.

Eight wrestlers have won the Royal Rumble match twice, but did you know who won it three times?