The Rumble kicks off the year in a big way, and there is plenty of excitement surrounding it, considering it is the official start on the road to WrestleMania. Entering the Royal Rumble match at number one is a often privilege, however, it has been proven to be extremely difficult to win the Rumble from that spot!
However, Shawn Michaels in 1995 and Chris Benoit in 2004 have the distinction of being the only men to outlast 29 other competitors and win the Royal Rumble from the number one position. Nonetheless, many wrestlers have put in valiant efforts worthy of winning the Rumble as the first entrant but to no avail.
10 Eddie Guerrero - 2005
The 2005 Royal Rumble marked Eddie Guerrero's final appearance in a Royal Rumble match before his untimely death at the age of 38 in November. Latino Heat began the match with his best friend Chris Benoit, who won the Rumble the year prior. Guerrero and Benoit wowed the crowd with their sublime in-ring technical wrestling.
Guerrero lasted a little over 28 minutes in the match, and he collaborated with Benoit to eliminate Hardcore Holly. Eddie also paired up with Rey Mysterio to toss over Booker T, and Eddie sent The Hurricane packing. Ultimately, Edge ended Guerrero's chances of competing for a World Championship at WrestleMania 21.
9 The Undertaker - 2008
At the 2007 edition of the Royal Rumble, The Undertaker made history by becoming the first man to win the Royal Rumble as the 30th entrant. A year later at the 2008 Royal Rumble, for The Undertaker to replicate his success, he started from the number one spot. The Rumble picked up right where it left off, as Undertaker eliminated Shawn Michaels to win the Rumble, and HBK was the second entrant in 2008.
Undertaker spent 32 minutes in this match, and his outing was not as impressive as his 2007 victory. He eliminated just three superstars this time around with Santino Marella and The Great Khali barely making an impression. Snitsky was Undertaker's third victim before HBK halted Undertaker's chances of joining the exclusive back-to-back Royal Rumble winners club.
8 Ted DiBiase - 1990
Ted DiBiase will go down in history as one of the greatest to never win the WWE Championship. DiBiase set a record at the 1990 Royal Rumble with the longest time in a Royal Rumble match at 44:47.
That seems like light work with many wrestlers eclipsing that total in later years. The Million Dollar Man scored the first two eliminations by ending Koko B.Ware and Marty Jannetty's hopes within the first two minutes. He aided five others to send Earthquake home but The Ultimate Warrior halted DiBiase's progress.
7 CM Punk - 2014
January 26, 2014, is the date of the Royal Rumble that year. More significantly, it is also the final time that CM Punk wrestled in a WWE ring. The Second City Saint entered the Royal Rumble match as the number one participant for the second time in four years.
Punk was looking to bounce back from disappointing losses to the likes of The Rock, The Undertaker, and Brock Lesnar in huge PPV matches in 2013. Despite reaching the final four, Kane returned and pulled Punk over the top rope. Adding insult to injury, Kane chokeslammed Punk through the announce table, which signaled the end of Punk's WWE career.
6 Sasha Banks - 2018
Undoubtedly, Sasha Banks was the standout performer in the inaugural women's Royal Rumble match in 2018. The Boss also was the very first participant to enter the women's Royal Rumble in a historic moment. Sasha endured 54:46 of action, which is simply sensational.
Banks squared off with Trish Stratus, which was an exciting moment and Trish was one of the three entrants that Sasha eliminated from the Rumble. However, Sasha's efforts were not enough as she reached the final four but the Bella Twins ended Banks' quest of heading to WrestleMania 34.
5 CM Punk - 2011
The 2011 Royal Rumble was an eventful night for CM Punk. The leader of the New Nexus cost Randy Orton the chance at regaining the WWE Championship from The Miz. Nevertheless, the Second City Saint had his own business to attend to as the number one entrant in the Rumble, which was the first-ever 40-man Royal Rumble match.
Drama ensued before the match even began as Punk's New Nexus brawled with Wade Barrett's Corre. Moreover, the New Nexus helped Punk last 35:21 with the Straight Edge Savior earning a whopping seven eliminations. It was a missed opportunity as John Cena eliminated Punk with ease but Punk was in prime position to main event WrestleMania XXVII.
4 Roman Reigns - 2016
At the 2016 Royal Rumble, Roman Reigns defended the WWE World Heavyweight Championship in a 30-man Royal Rumble match. Mr. McMahon and The Authority punished Reigns, who brutalized Triple H at TLC 2015, to put him in a difficult situation.
To remain as the WWE World Heavyweight Champion, Reigns had to outlast 29 other superstars. It was a tremendous outing from the Big Dog, who was certainly not popular with the fans. Reigns eliminated five superstars and lasted a few seconds shy of an hour. Triple H returned as the 30th entrant, and the Game received a huge pop when he tossed over Reigns, and he went on to clinch a 14th World Championship by eliminating the Intercontinental Champion Dean Ambrose.
3 Stone Cold Steve Austin - 1999
Stone Cold Steve Austin was aiming to win his third consecutive Royal Rumble match at the 1999 Royal Rumble. The Texas Rattlesnake entered first and his longtime rival Mr. McMahon stared across the ring as the second entrant. Austin's night was very interesting, to say the least. McMahon put a $100,000 bounty for anyone who could eliminate Stone Cold.
After Stone Cold dispatched Golga, McMahon lured Austin backstage as The Corporation was in on the dastardly plan, executing it by taking out Austin. Stone Cold was sent to the hospital but he returned by raising hell, eliminating seven more wrestlers. Ultimately, The Rock with his newly won WWF Championship in tow, distracted Stone Cold which allowed McMahon to eliminate Austin for a Rumble victory in his first attempt.
2 Brock Lesnar - 2020
Brock Lesnar declared himself as the number one participant in the 2020 Royal Rumble match. The announcement was shocking in itself as the Beast Incarnate was the reigning WWE Champion. Lesnar decimated the field and it was like he was toying with his prey.
Lesnar eliminated an impressive 13 wrestlers, which is a record (if you don't count Braun Strowman's 13 in the Greatest Royal Rumble). However, Lesnar was unable to build on his momentum as Drew McIntyre brought an end to his dominance. To the delight of the crowd, McIntyre's Claymore Kick sent Lesnar packing, and the Scottish Psychopath went on to win the Rumble and end Lesnar's reign as WWE Champion at WrestleMania 36.
1 Triple H - 2006
Triple H was desperate to return to the main event of WrestleMania by entering the 2006 Royal Rumble match as the number one entrant. The Game opened up proceedings with the eventual winner Rey Mysterio. Moreover, the Game had a lot of enemies in this Rumble as he feuded with Big Show and Ric Flair.
Nonetheless, Triple H managed to eliminate both Show and Flair early on. He also eliminated Show's World Tag Team Championship partner Kane and Chavo Guerrero. Regardless of being a heel, he formed a brief alliance with Mysterio, and the duo collaborated to eliminate Simon Dean and Rob Van Dam. However, Triple H's former Evolution stablemate Randy Orton was the final entrant, and the two teamed up against Mysterio. The master of the 619 thwarted Triple H's chances of second Rumble victory with the Game lasting an hour, which is a testament to his conditioning. Mysterio went on to win the match and the World Heavyweight Championship at WrestleMania 22.