The Undertaker

Undertaker’s 7 Best & 7 Worst Matches At The Royal Rumble

The Undertaker has had an up and down career at the Royal Rumble. There were big wins, epic clashes, bad matches, and some embarrassing moments.

The Undertaker has been one of the best performers in Royal Rumble history. The Deadman will go down in history as one of the all-time greats to grace a WWE ring due to his longevity and passion for the business.

Furthermore, the Royal Rumble has been one of The Undertaker’s most testing events, especially in the ’90s with a mixed bag of results. Nonetheless, Undertaker has created many great moments at the Rumble with the highlight being in 2007, when he finally won the Royal Rumble match. Still, there were highs and lows overall.

Updated on January 10th, 2022 by Tevon King: The Royal Rumble is one of the most prestigious events on the WWE calendar and The Undertaker has been involved in 19 matches at the titular event. The Undertaker has a good win-loss record throughout his 30-year WWE career but his Rumble record is underwhelming for his standards. The Phenom has registered just six wins, and he has lost 13 times at the Rumble. However, he has participated in 11 Royal Rumble matches with one triumph to his name in 2007. Whilst, Undertaker is one of the all-time greats, not all of his Royal Rumble appearances have been memorable. He has contested some outstanding World Championship matches at the Royal Rumble with mixed win/loss results. The Undertaker has also been involved in a plethora of different gimmick matches at the Rumble, and he has been an integral part of the Rumble’s success.

14 * Worst: Royal Rumble Match – 1992

This entry comes with a caveat as despite the 1992 Royal Rumble match is possibly the best ever, Undertaker’s performance in the match leaves a lot to be desired. The Undertaker competed in the Royal Rumble match for the second time in 1992, and it was for the vacant WWE Championship. The Phenom entered the titular bout as the 20th entrant and he immediately shoved “Superfly” Jimmy Snuka over the top rope for his sole elimination.

Undertaker shifted his attentions towards the man who helped him win the WWE Championship in the first place, Ric Flair. It wasn’t the best outing for Undertaker although he saved Jake Roberts from Randy Savage’s clutches. The Deadman endured just under 14 minutes until Hulk Hogan clotheslined him over the top rope and stopped him from reclaiming the WWE Title.

13 * Best: Royal Rumble Match – 2001

There’s no greater sight than seeing The Undertaker and Kane working as a cohesive unit. The Brothers of Destruction reunited in the 2001 Royal Rumble match, and they were a force to be reckoned with.

Undertaker joined the fray as the 25th participant, and he immediately came to his brother Kane’s aid. They cleaned out the house with Undertaker eliminating Bradshaw, Hardcore Holly, and Val Venis. Scotty 2 Hotty was the next unfortunate casualty as he ran into the Brothers of Destruction who showed no mercy. Ultimately, Rikishi entered last and he eliminated Undertaker with a savate kick for a surprising elimination.

12 * Worst: Royal Rumble Match – 1997

The Undertaker pulled double duty at the 1997 Royal Rumble, and it was a Rumble to forget for the Deadman. However, Undertaker entered the 1997 Royal Rumble match from the luxurious 30th position, and he was looking to main event WrestleMania for the first time.

Undertaker immediately went after his rivals Vader and Mankind. He planted both Vader and Steve Austin with a Chokeslam. Henry Godwinn felt Undertaker’s wrath by flinging him over the top rope with ease. The Deadman nailed Mankind with a big boot for another elimination. Nevertheless, Undertaker would be screwed over as Austin got eliminated but the referees failed to see it allowing Austin to worm his way back into the ring by eliminating both Undertaker and Vader en route to winning the Rumble.

11 * Best: Royal Rumble Match – 2008

Just how the 2007 Royal Rumble match ended, it started the same way with The Undertaker and Shawn Michaels kicking things off in the 2008 Royal Rumble match. The Demon of Death Valley had to go through the scenic route if he was going to become a back-to-back Royal Rumble match-winner.

Undertaker’s performance didn’t reach the heights of 2007 but it was another valiant effort from the former World Champion. The likes of Santino Marella, The Great Khali, and Snitsky were eliminated by Undertaker. Moreover, Undertaker lasted 32 minutes and it was HBK who halted his progress with Sweet Chin Music.

10 Worst: The Undertaker Vs. Yokozuna – 1994

The feud between The Undertaker and Yokozuna heated up in the Survivor Series elimination match in 1993. Yokozuna was the reigning WWE Champion, and at the 1994 Royal Rumble, he defended his title against Undertaker in a casket match.

Yokozuna was deathly afraid of caskets, and a double-wide casket was made for him. Unfortunately, their match was a wreck as Yokozuna was immobile in the ring. Nonetheless, Yokozuna retained the title after many wrestlers came down to ringside to beat up Undertaker and put him in the casket. The Deadman was not to be seen again until SummerSlam.

Best: Royal Rumble Match – 2002

The Undertaker turned heel in 2001 and he entered the 2002 Royal Rumble match as the WWE Hardcore Champion. Business picked up when Undertaker became the eighth entrant, and he was in no mood to hang around.

Undertaker eliminated Rikishi, Goldust, Al Snow, and Billy Gunn. He had a brief altercation with the Hardy Boyz, and he eliminated both of them. However, in one of the biggest shocks in Rumble history, Maven eliminated Undertaker with a dropkick. It was the biggest mistake that Maven would make as Undertaker angrily reacted by eliminating him and left him a bloody mess, even dumping his head into popcorn in the concession stands.

Worst: The Undertaker Vs. Vader – 1997

Another low moment for The Undertaker came at the 1997 Royal Rumble when he took on Vader. Vader had an up and down career in WWE but hoped that he could rejuvenate things with a massive victory over Undertaker.

Undertaker’s former manager Paul Bearer came down to ringside and he nailed The Undertaker in the head with the urn. Vader picked up a surprising victory over Undertaker with the Vader Bomb and Vader became Bearer’s latest client afterward. Nonetheless, it was a plodding affair and Undertaker suffered his first pinfall defeat at the Rumble.

Best: The Undertaker Vs. Rey Mysterio – 2010

The Undertaker defended a championship for the first time at the Royal Rumble in 2010. The Deadman was the reigning World Heavyweight Champion, while fellow former Royal Rumble winner Rey Mysterio was the challenger.

Undertaker always works well with smaller guys, and this clash was no different. The ultimate underdog in WWE history was closing in on a second world championship reign with two 619s. However, Undertaker superbly countered Mysterio’s West Coast Pop into maybe the best Last Ride of his career and retained the title in an enthralling encounter.

Worst: The Undertaker Vs. Irwin R. Schyster – 1995

The Undertaker’s bad run of luck with disastrous feuds in the early part of his career continued in 1995 as the Deadman began feuding with Ted DiBiase’s Million Dollar Corporation. Undertaker squared off with DiBiase’s right-hand man Irwin R. Schyster in a dismal affair.

The pace of the match was very slow and methodical. Nevertheless, the Phenom scored his first pinfall victory at the Rumble with a Chokeslam on IRS. Furthermore, Undertaker’s WrestleMania 11 clash with King Kong Bundy was set up as Bundy assaulted Undertaker, which allowed IRS to steal the urn from Paul Bearer.

Best: The Undertaker Vs. Bret Hart – 1996

For the third time in six years, The Undertaker competed for the WWE Championship at the Royal Rumble. Bret Hart’s reign was in huge jeopardy with Undertaker as the challenger. Before the match, Diesel was on the way to the locker room after losing out to Shawn Michaels in the Rumble match, and he had an altercation with The Undertaker.

When the action got underway, both men displayed heelish tendencies despite being faces. The Hitman tore off Undertaker’s Phantom of the Opera mask in the match and worked on his leg. Undertaker was closing in on a second WWE Championship with a jaw-dropping Tombstone. However, Diesel returned and cost Undertaker the match with Undertaker picking up the win by way of disqualification, planting the seeds for their WrestleMania 12 encounter.

Worst: The Undertaker Vs. Heidenreich – 2005

Heidenreich cost The Undertaker the chance of winning the WWE Championship twice from John Bradshaw Layfield at No Mercy and Armageddon 2004. Sandwiched in between those matches, Undertaker defeated Heidenreich in a lackluster match at Survivor Series.

Their feud culminated in Undertaker’s specialty, a casket match at the 2005 Royal Rumble. Heidenreich was a terrible worker, and Undertaker tried to get him over but it did not work. Raw‘s Snitsky got involved to aid Heidenreich but Undertaker’s brother Kane emerged from the casket and battled with Snitsky into the crowd. Undertaker put the finishing touches on this horrific casket match by nailing Heidenreich with a Tombstone Piledriver and rolling him into the casket.

Best: Royal Rumble Match – 2007

The Demon of Death Valley was bidding to become the first man to win the Royal Rumble match from the number 30 spot. The Undertaker had never won the match in his illustrious career and he was determined to put that right.

The Phenom immediately stamped down his authority by eliminating MVP and The Great Khali. Once Shawn Michaels eliminated Randy Orton and Edge, it was down to the two legends to fight it out. Undertaker and Michaels slugged it out, which had fans on the edge of their seat but Undertaker outlasted HBK to win the Rumble for the first time. He went on to defeat Batista in their World Heavyweight Championship clash at WrestleMania 23.

Worst: Royal Rumble Match – 1993

The 1993 Royal Rumble was the first to award the winner a WWE Championship match in the main event of WrestleMania. The Undertaker was the 15th entrant and was a formidable force.

The Deadman eliminated Ted DiBiase, Genichiro Tenryu, Samu, and The Berzerker. However, many will feel that Undertaker was robbed as the Giant Gonzalez made his WWE debut. He was not involved in the Rumble but he assaulted The Undertaker and eliminated him from the match, with Undertaker’s brief cameo only lasting four minutes. Unfortunately, it was the start of a dismal feud between the two, which lasted for the better part of seven months.

Best: The Undertaker Vs. Shawn Michaels – 1998

Shawn Michaels accidentally cost The Undertaker the WWE Championship at SummerSlam 1997, which led to a sensational rivalry between them. HBK controversially captured his third WWE Championship from Bret Hart at the Survivor Series. Michaels had a stern challenge in The Undertaker at the 1998 Royal Rumble with the title being defended in a casket match. This is by far the best casket match in WWE history and both men shined in this spectacular clash.

Unfortunately, Undertaker’s woes in WWE Championship matches at the Royal Rumble continued as he failed to capture the title for the third time. Kane interrupted and chokeslammed him in the casket which allowed HBK to retain the WWE Championship. This match is also notable for Michaels, injuring his back after his back caught the back edge of the casket but he still managed to soldier on and perform at an extremely high level.

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