Winning the Royal Rumble match is one of the hardest accomplishments to pull off in professional wrestling. The match only comes around once a year, and only one (two in 1994) person can win it.
There are plenty of huge names who have never won a Rumble match, including Randy Savage, CM Punk, Ultimate Warrior, Andre The Giant, Chris Jericho, Daniel Bryan, Big Show, and more, with that showing just how tough it can be. There have been some occasions of a wrestler winning multiple Royal Rumbles, though the quality of their victories can vary, with some multi-time winners being far better than others.
9 Brock Lesnar
It must be said that Brock Lesnar’s first Royal Rumble victory was a good moment, with it signaling the next step of his on the way to superstardom, overcoming his heated rival The Undertaker in the final two. He did enter quite late in 2003, so it wasn’t the most impressive showing, though he would go on to win the WWE Title from Kurt Angle.
What makes Lesnar arguably one of the worst multi-time Rumble winners is 2022, with him being the most predictable and uninspiring winner of the most boring Rumble match ever. With him being a part-time winner, it lacked all creativity.
8 Batista
In 2005, Batista’s Royal Rumble win was a true star-making moment, though the ending was botched as both he and John Cena tumbled over the top rope in an unplanned moment. Batista would ultimately win and then defeat Triple H after a brilliant babyface rise to win the World Title.
Unfortunately, Batista’s second Rumble victory is among the most unpopular decisions ever. Despite being a returning icon, he was booed out of the building as he won the match, with fans instead wanting Daniel Bryan. Thankfully, things turned out as Batista turned heel and Daniel Bryan won in the WrestleMania main event, so overall this wasn’t as bad as it could’ve been.
7 Randy Orton
Both of Randy Orton’s Royal Rumble wins were both just “fine”. In 2009, he was a hot act, and he used his Legacy faction to aid him to win the match, though it came after a very slow and basic Rumble contest.
In 2017, the Rumble was stacked with big names, and it was Orton who won. However, this came at the expense of Bray Wyatt, who would have been a far better choice. Orton did get a big pop as he dumped out Roman Reigns, and he would go on to win the WWE Title (which he failed to do in 2009), but it was all just “meh”.
6 John Cena
John Cena’s return and victory in the 2008 Royal Rumble is one of the greatest WWE moments of all time, with him overcoming all the odds to return from injury. He didn’t win the WWE Title at WrestleMania, but his Rumble victory was incredible.
In 2013, Cena was unfortunately the only conceivable choice to win due to a lack of star power, in one of the most predictable winners ever. It was a very underwhelming Rumble and victory, though for a name like Cena, who is among the very greats, two Rumble wins makes sense to add to his legacy.
5 Triple H
Triple H entered the 2002 Rumble as the odds on favorite after a huge babyface return. He put in a very strong showing, lasting over 20 minutes and last eliminating Kurt Angle.
In 2016, he was greeted with a massive reaction as he went on to win the WWE Championship due to it being on the line, however in hindsight, booking a full-time wrestler to win would have been far better, and his match at WrestleMania against Roman Reigns was very poor.
4 Hulk Hogan
In the early days of the Royal Rumble, Hulk Hogan was a very dominant competitor. His first win came in 1990, overcoming a sea of strong competitors, lasting over 20 minutes and eliminating six men.
He became the first ever back-to-back Rumble winner the following year. Hogan put in a similar performance of over 20 minutes and several eliminations, and the crowd were very much into him winning. At the time, he was the number one star, so it made sense to have him be a multi-time winner, even if other wrestlers would have no doubt benefited.
3 Edge
Edge has had some of the best Rumble moments ever. In 2010, he made a shocking return from injury, winning the match in quick fashion, though the finale of the Rumble was a lot of fun.
In 2021, Edge entered at number one, becoming just the third man to ever pull off the feat of winning the match from that position. His performance was great, and his win came out of left field, going on to main event WrestleMania in a terrific title match. On both occasions, he fell short of winning World Title gold though.
2 Shawn Michaels
Shawn Michaels was the second ever back-to-back Rumble winner, and on both occasions he put in a very good performance. He holds the reputation of being the first ever Rumble winner to come from the number one spot, doing so in 1995 with a memorable win and false finish.
The following year, even though he entered much later at number 18, he still lasted for a very strong 26 minutes, and for the second year in a row eliminated 8 men. This time around, he would win the WWE Championship at WrestleMania in a classic Iron Man match against Bret Hart.
1 Steve Austin
With an unprecedented three Royal Rumble victories, there can be no one else in the top spot. Steve Austin’s first win came in 1997 when he cheated his way to victory, returning to the ring after elimination. Though he was stripped of his title shot, it would lead to one of the greatest WrestleMania matches ever against Bret Hart.
The following year, this time as the hottest babyface in WWE, he won the Rumble again in incredibly dominant fashion, with his eventual title win further aiding WWE into the Attitude Era. Finally, in 2001, Austin won one of the most enjoyable Rumbles ever, winning the match to a massive ovation before going on to win the WWE Title in arguably the greatest WrestleMania PPV of all time.