At Survivor Series 1990,The Undertaker made his legendary WWE debut, and he retired 30 years later to the day at Survivor Series in 2020. The Deadman is a seven-time World Champion, and he has headlined countless WrestleMania's. However, the Royal Rumble has proven to be a testing event for Undertaker over the years. The Demon of Death Valley has won the Royal Rumble once in 2007, and he converted that into a World Championship win at WrestleMania 23.

RELATED: The Undertaker: Top 10 Wrestlers He's Faced The Most

He has been a runner-up once in 2003 but he endured some embarrassing moments at the Rumble. Undertaker has been a victim of some surprising eliminations but that has not hampered his career. Moreover, Undertaker boasts the second most collective Rumble eliminations in WWE history with 44 after his brother Kane. The Deadman has often found himself at the business end at the Royal Rumble which is a testament to his quality.

UPDATE: 2023/01/25 07:00 EST BY TEVON KING

The Undertaker is one of the greatest wrestlers of all time. The Demon of Death Valley had a remarkable WWE career, and he earnt his rightful spot in the WWE Hall of Fame in 2022. Whilst Undertaker had tremendous success at WrestleMania, he also had some memorable moments at the Royal Rumble. Undertaker competed in 11 Royal Rumble matches throughout his WWE career. He won the Royal Rumble match once, and he was runner-up once. Nonetheless, Undertaker has been dominant in some Royal Rumble matches by registering multiple eliminations, and there were other times when he didn't have a long stint in the titular bout It's a big deal when someone eliminates Undertaker from a Royal Rumble match as he is a marquee name in the wrestling business.

11 1993

The Undertaker Royal Rumble 1993 Cropped

The Undertaker competed in the 1993 Royal Rumble match, and this was the first year that the winner of the Royal Rumble would be awarded a World Championship match at WrestleMania. The Deadman emerged through the curtains as the 15th entrant.

Things ran smoothly for Undertaker as he eliminated Ted DiBiase, Genichiro Tenryu, Samu, and The Berzerker from the match. He was one of the favorites to win the Rumble but a debuting Giant Gonzalez made his WWE debut. He towered over Undertaker and despite not being an official entrant, he assaulted Undertaker and eliminated him.

The Undertaker's 1993 Royal Rumble Match Statistics:

Entry Number: 15

Eliminations: Samu, Genichiro Tenryu, Ted DiBiase, The Berzerker

Eliminated By: Giant Gonzalez

Time Spent In Royal Rumble Match: 4 minutes and 14 seconds

10 1997

The Undertaker Royal Rumble 1997 Cropped

At Royal Rumble 1997, The Undertaker pulled double duty, and he was looking to bounce back from losing to Vader in a hard-hitting match earlier on in the night. The Deadman drew the luxurious number 30 position in the 1997 Royal Rumble match.

Undertaker lasted just under seven minutes, and he ferociously eliminated Henry Godwinn and he sent his rival Mankind packing. Ultimately, Undertaker was one of Steve Austin's victims as Austin snuck back into the Rumble and he hauled over both Undertaker and Vader on his way to winning the Royal Rumble match.

The Undertaker's 1997 Royal Rumble Match Statistics:

Entry Number: 30

Eliminations: Henry O. Godwinn, Mankind

Eliminated By: Steve Austin

Time Spent In Royal Rumble Match: 6 minutes and 46 seconds

9 1992

The Undertaker Royal Rumble 1992 Featured Image Cropped

The Undertaker was looking to reclaim the WWE Championship in the 1992 Royal Rumble match. It was the first time that the WWE Title would be contested in a Royal Rumble match. The Deadman was the 20th entrant and made an impact as he eliminated his first WrestleMania streak victim "Superfly" Jimmy Snuka for his sole elimination.

Undertaker was more focused on matters on the outside as he had to save Jake Roberts from Randy Savage's clutches. Moreover, Undertaker lasted just 14 minutes, and the man who beat him for the WWE Title, Hulk Hogan removed him from the equation with a clothesline over the top rope.

The Undertaker's 1992 Royal Rumble Match Statistics:

Entry Number: 20

Eliminations: Jimmy Snuka

Eliminated By: Hulk Hogan

Time Spent In Royal Rumble Match: 13 minutes and 51 seconds

8 1991

Undertaker Royal Rumble 1991 Cropped

For the first time in his career, The Undertaker competed in a Royal Rumble match at the 1991 Royal Rumble. Undertaker joined the fray as the 12th participant, and it wasn't a bad way to open up your Royal Rumble legacy by eliminating Bret Hart.

He registered two more eliminating with Bushwhacker Butch and The Texas Tornado feeling the wrath of the Deadman. However, Undertaker's movement was languid around the ring, and the Legion of Doom nailed Undertaker with a double clothesline that sent him crashing onto the outside.

The Undertaker's 1991 Royal Rumble Match Statistics:

Entry Number: 12

Eliminations: Bret Hart, Bushwhacker Butch, The Texas Tornado

Eliminated By: Hawk & Animal

Time Spent In Royal Rumble Match: 14 minutes and 16 seconds

7 2017

The Undertaker Royal Rumble 2017 Cropped

The Undertaker participated in the Royal Rumble match for the final time in 2017, and he was the penultimate entrant by entering 29th. Undertaker played mind games as he snuck up behind Goldberg, and eliminated Baron Corbin.

RELATED: 10 Ways These Classic Royal Rumble Matches & Moments Have Aged Poorly

Undertaker retaliated after Goldberg speared him by removing him from the Rumble. However, Undertaker failed to eliminate Roman Reigns, and after Undertaker chokeslammed Chris Jericho, Reigns threw Undertaker over the top rope. Fans were fuming and Reigns eliminated him which drew a chorus of boos and it planted the seeds for their WrestleMania 33 encounter.

The Undertaker's 2017 Royal Rumble Match Statistics:

Entry Number: 29

Eliminations: Baron Corbin, Goldberg, The Miz, Sami Zayn

Eliminated By: Roman Reigns

Time Spent In Royal Rumble Match: 8 minutes and 46 seconds

6 2009

The Undertaker Royal Rumble 2009 Cropped

At Royal Rumble 2009, The Undertaker joined the Royal Rumble match as the 16th entrant. Everyone stopped wrestling once Undertaker made his presence felt. The Phenom eliminated both JTG and Shelton Benjamin from the match.

However, the Demon of Death Valley's head was busted wide open. Undertaker survived Jericho's Codebreaker, and he snuck up behind Jericho and he eliminated him. Again, Undertaker was screwed as he fended off Legacy but Big Show pulled him off the apron to halt his quest of headlining WrestleMania again.

The Undertaker's 2009 Royal Rumble Match Statistics:

Entry Number: 16

Eliminations: JTG, Mark Henry, Shelton Benjamin, Chris Jericho

Eliminated By: Big Show

Time Spent In Royal Rumble Match: 33 minutes and 30 seconds

5 2003

Undertaker interacting with Brock Lesnar during Rumble 2003

The Undertaker competed in a Royal Rumble match as the 30th entrant for the second time in his career at the 2003 Royal Rumble. Undertaker still had not won a Royal Rumble match but he had a superb chance of putting that to an end.

Undertaker wasted no time in cleaning out the house by throwing John Cena, Jamal, and Batista over the top rope. Maven tried to eliminate Undertaker for the second year in succession but that failed. Undertaker got his revenge by removing Maven from the equation. Undertaker then turned on his brother Kane for another elimination, but he was unable to get the better of his SmackDown colleague Brock Lesnar, who eliminated him to win the Rumble for the first time of his career.

The Undertaker's 2003 Royal Rumble Match Statistics:

Entry Number: 30

Eliminations: John Cena, Jamal, Maven, Batista, Kane

Eliminated By: Brock Lesnar

Time Spent In Royal Rumble Match: 6 minutes and 45 seconds

4 2001

Rikishi Royal Rumble 2001 Cropped

It spelled bad news for the rest of the field in the 2001 Royal Rumble match when The Undertaker and Kane were on the same page. Undertaker entered the Rumble in his American Badass gimmick for the first time, and he immediately aided Kane who was outnumbered.

RELATED: The 5 Best Things About The 2001 Royal Rumble (& 5 Worst)

Undertaker eliminated Bradshaw, Hardcore Holly, and Val Venis. The Brothers of Destruction were in the ring on their lonesome with Scotty 2 Hotty entering at a bad time. Undertaker and Kane showed no mercy and they eliminated Scotty from the match. Ultimately, Rikishi halted Undertaker's dominance by surprisingly eliminating him with a savate kick.

The Undertaker's 2001 Royal Rumble Match Statistics:

Entry Number: 25

Eliminations: Bradshaw, Hardcore Holly, Val Venis, Scotty 2 Hotty

Eliminated By: Rikishi

Time Spent In Royal Rumble Match: 10 minutes and 45 seconds

3 2008

The Undertaker Royal Rumble 2008 Cropped

Two legends in The Undertaker and Shawn Michaels renewed their rivalry by starting the 2008 Royal Rumble match. The Deadman was the number one participant in a Royal Rumble match for the first time in his legendary career.

Undertaker was aiming to join Hulk Hogan, Steve Austin, and Michaels himself as back-to-back Rumble winners. That failed to materialize but it was a good effort from Undertaker as he eliminated Santino Marella, The Great Khali, and Snitsky. The Heartbreak Kid eliminated Undertaker with Sweet Chin Music, and Undertaker endured a respectable 32 minutes of action.

The Undertaker's 2008 Royal Rumble Match Statistics:

Entry Number: 1

Eliminations: Santino Marella, The Great Khali, Snitsky

Eliminated By: Shawn Michaels

Time Spent In Royal Rumble Match: 32 minutes and 33 seconds

2 2002

The Undertaker Royal Rumble 2002 Cropped

The 2002 Royal Rumble match predictably went Triple H's way but the first half of the Royal Rumble match belonged to The Undertaker. The Undertaker was the reigning Hardcore Champion, and he entered the match eighth in a foul mood.

Rikishi, Goldust, Al Snow, and Billy Gunn were easily dismissed by Undertaker. Moreover, Undertaker briefly feuded with the Hardy Boyz, and they rallied against him but it proved to be futile. However, Tough Enough winner Maven stunned Undertaker with a dropkick to the back for an elimination which produced one of the biggest shocks in Royal Rumble history. It proved to be unwise as Undertaker viciously assaulted Maven with a sickening chair shot to the head, and he pummeled him around the arena.

The Undertaker's 2002 Royal Rumble Match Statistics:

Entry Number: 8

Eliminations: Goldust, Al Snow, Rikishi, Billy, Jeff Hardy, Matt Hardy, Maven

Eliminated By: Maven

Time Spent In Royal Rumble Match: 7 minutes and 40 seconds

1 2007

Shawn Michaels Royal Rumble 2007 Cropped

The 2007 Royal Rumble match presented another opportunity for The Undertaker to finally win the Royal Rumble match. Just like he did in 2003, he entered the Royal Rumble match from the favorable number 30 position.

The Undertaker flung MVP and The Great Khali over the top rope for his first couple of eliminations to get settled down. To cap it off, the ending was one of the greatest in Royal Rumble history. Two-time Royal Rumble winner Shawn Michaels and Undertaker went back and forth which had fans on the edge of their seats. Taker averted Michaels' Sweet Chin Music, and he hauled him over the top rope to win the Rumble for the first time and he became the first Royal Rumble winner to win from the number 30 spot.

The Undertaker's 2007 Royal Rumble Match Statistics:

Entry Number: 30

Eliminations: The Great Khali, MVP, Shawn Michaels

Final Position: Winner

Time Spent In Royal Rumble Match: 13 minutes and 15 seconds