5 Biggest Allies Of The Undertaker's Wrestling Career (& 5 Biggest Enemies)
Mia Walsh
Published Mar 28, 2026
Unquestionably, The Undertaker is one of the greatest wrestlers of all time. The Demon of Death Valley had a long WWE career that spanned three decades. Undertaker's wrestling career has been successful and he had success as both a babyface and as a heel. The Undertaker has had his fair share of injuries that have kept him out of the squared circle, but Undertaker has always bounced back in style.
RELATED: 10 Wrestlers The Undertaker Couldn't Get Over
Undertaker has generally been on his lonesome for a chunk of his WWE career and feuding with Undertaker has been pivotal for some wrestlers who managed to go to the next level. Whilst, Undertaker has had many souls to bury throughout his illustrious career, he has also had some handy allies by his side.
10 Biggest Enemy: Brock Lesnar
The rivalry between The Undertaker and Brock Lesnar began in 2002 when Lesnar captured the WWE Championship from The Rock at SummerSlam. Undertaker and Lesnar had good chemistry together and they knocked it out of the park in a violent Hell in a Cell match at No Mercy with Lesnar retaining the WWE Championship.
Lesnar got the better of Undertaker once more at No Mercy 2003 in a Biker Chain match to remain as WWE Champion. However, they renewed old hostilities in 2014 with Lesnar shocking the world when he ended Undertaker's 21-0 WrestleMania unbeaten streak at WrestleMania 30. They had a rematch at SummerSlam 2015 which Undertaker triumphed, but Lesnar got the last laugh at Hell in a Cell 2015 in another Hell in a Cell match between the pair.
9 Biggest Allies: The Acolytes
The Undertaker's Ministry of Darkness stable began to take shape in late 1998 and early 1999 with the Acolytes as his first recruits. Bradshaw and Faarooq were The Undertaker's trusted henchmen and they hardly put a foot wrong under Undertaker's leadership.
The Acolytes helped Undertaker recruit Mideon, Viscera, and the Brood comprised of Edge, Christian, and Gangrel to join the Ministry of Darkness. The Acolytes were by Undertaker's side when the Ministry fused with the Corporation to become the Corporate Ministry, and the Acolytes brought the WWE World Tag Team Championship to the group whilst Undertaker was holding the WWE Championship.
8 Biggest Enemy: Edge
One of The Undertaker's major rivals was Edge, and the Rated-R Superstar proved to be a thorn in The Undertaker's side. Edge beat Undertaker for the World Heavyweight Championship by cashing in his Money in the Bank briefcase in May 2007.
Edge and Undertaker headlined WrestleMania 24 with the Deadman seeing off Edge to win his second World Heavyweight Championship. They continued to have intriguing battles in 2008 with Edge beating Undertaker in a TLC match at One Night Stand, and their rivalry came to a halt at SummerSlam with Undertaker defeating Edge in a Hell in a Cell match.
7 Biggest Ally: Steve Austin
The Undertaker and Steve Austin were major rivals in the Attitude Era as they battled over the WWE Championship and they had an upcoming collision course at SummerSlam 1998. However, at Fully Loaded: In Your House, Undertaker and Austin defeated Undertaker's brother Kane and Mankind for the WWE World Tag Team Championship.
RELATED: Every Stable & Tag Team That Steve Austin Was Part Of, Ranked Worst To Best
This was Undertaker's first Tag Team Championship reign, and he departed with both Tag Team Championships on his shoulders. Despite being rivals, Undertaker and Austin managed to co-exist briefly, but their title reign lasted under two weeks with Kane and Mankind regaining the titles in a fatal-4-way tag team match on Raw.
6 Biggest Enemy: Shawn Michaels
Everyone remembers The Undertaker and Shawn Michaels' rivalry from their two WrestleMania epics at WrestleMania 25 and WrestleMania 26 but their first major feud was toward the end of the New Generation Era. Michaels cost Undertaker the WWE Championship at SummerSlam 1997 as he was the special guest referee and he clocked him across the face with a steel chair.
Undertaker and Michaels contested the first-ever Hell in a Cell match with the Heartbreak Kid prevailing. Their matches were exceptional as expected, but Michaels was robbed four years off his career as in their casket match for the WWE Championship at the 1998 Royal Rumble, Michaels herniated discs in his back as his back hit the casket. Undertaker sent Michaels into retirement at WrestleMania 26, but Michaels came out of retirement for one more match in the underwhelming tag team match between the Brothers of Destruction and DX at Crown Jewel 2018.
5 Biggest Ally: Big Show
After the Corporate Ministry quietly disbanded, The Undertaker took Big Show under his wing and they were unofficially called the "Unholy Alliance." The World's Largest Athlete needed a new direction and he wasn't going to get a better big man to learn from than The Undertaker.
Undertaker and Big Show had a successful alliance as they captured the WWE World Tag Team Championship twice. Their alliance was short-lived as Undertaker sustained an injury that ruled him out of action for the remainder of 1999.
4 Biggest Enemy: Kane
The rivalry between The Undertaker and Kane is one of the greatest stories ever told in WWE history. The Big Red Machine made his ominous debut at Badd Blood: In Your House during The Undertaker and Shawn Michaels' Hell in a Cell match.
RELATED: Every Kane Vs. Undertaker WWE Match, Ranked From Worst To Best
Undertaker and Kane had their long-awaited first meeting at WrestleMania 14 which Undertaker won and they had a rematch in an Inferno match which Undertaker won. The brothers battled several times throughout their careers, and they had a rematch at WrestleMania 20 with Undertaker prevailing once again. However, they had a trilogy of matches over the World Heavyweight Championship in 2010 with Kane winning all three tussles.
3 Biggest Ally: Paul Bearer
In early 1991, Brother Love handed over his managerial duties to Paul Bearer who managed The Undertaker for five-and-a-half years. They were the perfect double act with Bearer speaking in a high-pitched voice, and Undertaker being a man of few words.
Undertaker clinched his first WWE Championship under Bearer's guidance at Survivor Series 1991, and Bearer gained control of Undertaker by holding the urn. Their alliance shockingly ended at SummerSlam 1996 when Bearer betrayed Undertaker by siding with Mankind, but they reconciled two years later when Bearer backstabbed Kane to side with Undertaker. Undertaker and Bearer's entrance together was a sight to behold and they were one of the best client and managerial duos in WWE history.
2 Biggest Enemy: Mankind
On the Raw after WrestleMania 12, The Undertaker had a new nemesis to contend with and that was Mankind. Mrs. Foley's Baby Boy had success over Undertaker like no other wrestler enjoyed at this stage of their careers. Mankind beat Undertaker at King of the Ring 1996 and he replicated his victory at SummerSlam 1996 all thanks to Paul Bearer.
Mankind and Undertaker had some brutal matches over the years as they competed in the first-ever Buried Alive match. A year later, they clashed over the WWE Championship with Undertaker retaining the gold. Ultimately, their Hell in a Cell match at King of the Ring 1998 was infamous for Mankind taking some brutal bumps off the top of the cell and through the broadcast table. Mankind benefitted from working with Undertaker which led him to win the WWE Championship three times and a place in the WWE Hall of Fame in 2013.
1 Biggest Ally: Kane
Despite The Undertaker and Kane being on the opposite side of the ring, there have been times when The Undertaker and Kane have worked as a cohesive unit. The Brothers of Destruction are one of the most dominant tag teams in WWE history.
They formed at the 2001 Royal Rumble when they worked together in the Royal Rumble match, and they captured the WWE World Tag Team Championship twice and the WCW Tag Team Championship once in 2001. Undertaker and Kane had good chemistry together, and fans enjoyed watching the brothers working on the same side. They teamed up for the final time in 2018 in a losing effort to DX at Crown Jewel.
