The headline act of the WWE Hall of Fame class of 2022, The Undertaker has had a memorable career that is more than deserving of going into the WWE Hall of Fame alone. Nevertheless, Undertaker’s 30-year WWE career has been exceptional, and he has played a part in many wrestling fans’ childhood and into their adulthood. The Phenom has wrestled a plethora of matches, and there’s no way that every wrestling fan is going to remember every match that Undertaker has participated in.
Of course, his WrestleMania epics with Shawn Michaels, and the infamous Hell in a Cell match with Mankind at King of the Ring 1998 are going to live in infamy. Therefore, his memorable matches are more likely to be at the top of wrestling fans’ list, instead of the forgotten matchups.
10 The Undertaker Vs. The Executioner – In Your House: It’s Time, 1996
At the close of 1996, The Undertaker faced off with The Executioner in an Armageddon Rules match at In Your House: It’s Time. It was a Last Man Standing match, but you had to pin your opponent first, and they had to stay down for the count of 10.
It seemed nonsensical to pin your opponent first. Moreover, that rule was done away with afterward. However, Undertaker’s former manager Paul Bearer accompanied The Executioner to the ring. The match was underwhelming, and Undertaker saw off The Executioner with the Tombstone Piledriver doing the damage.
9 The Undertaker Vs. Kane – Raw (2/22/99)
The Undertaker and Kane faced off in the first Inferno match at Unforgiven: In Your House, 10 months later they locked horns in another Inferno match on Raw. Their second Inferno match is often forgotten about since it took place on Raw.
This was Undertaker’s first match in two months after his Buried Alive match with Steve Austin at Rock Bottom: In Your House. Undertaker and Kane’s matches became less special, and they failed to replicate their first Inferno match. Ultimately, the result remained the same with Undertaker beating Kane after Kane’s foot caught the fire.
8 The Undertaker Vs. Booker T – Judgment Day 2004
At WrestleMania 20, The Undertaker returned to his infamous Deadman gimmick. Undertaker sported the trench coat, black hat, and Paul Bearer was once again his manager. Two months later, The Undertaker was on a collision course with Booker T at Judgment Day 2004.
Booker turned heel after he joined SmackDown in the draft lottery. Undertaker and Booker’s feud was short-lived, and their match at Judgment Day was to get Undertaker back into the swing of things. The result was never in doubt with Undertaker seeing off Booker with the Tombstone.
7 The Undertaker Vs. Mankind – In Your House: Revenge Of The ‘Taker, 1997
Mankind is one of The Undertaker’s greatest rivals, and they have collided in a plethora of matches. One of their matches that goes under the radar is their WWE Championship match at In Your House: Revenge of the ‘Taker.
Undertaker recaptured the WWE Title at WrestleMania 13 a month prior, and Mankind was his first challenger. They hit a home run in an underrated gem of a WWE Championship match. Undertaker retained the WWE Title, and it was their final encounter until the iconic Hell in a Cell match at King of the Ring a year later.
6 The Undertaker Vs. Big Show – No Way Out 2003
The Undertaker and Big Show are two of the greatest big men in WWE history, and their paths crossed regularly. They feuded in the early part of 2003, and they were opponents at No Way Out. Their battle was physical, and neither man backed down.
Undertaker was busted wide open after Show headbutted him. However, A-Train interfered to give the World’s Largest Athlete some support. Their plans were thwarted as Undertaker’s Triangle Choke was enough to keep Show down and out.
5 The Undertaker Vs. Batista – TLC 2009
Arguably, The Undertaker and Batista’s rivalry was the feud of 2007 over the World Heavyweight Championship. Batista came out on top in their feud. Two years later, Batista turned heel, and he challenged Undertaker for the Big Gold Belt once again. This time, they were adversaries in a chairs match at TLC 2009.
This match often gets lost in the shuffle because of their sublime encounters in 2007. Moreover, this was still another excellent match between the pair. Batista thought he had reclaimed the World Heavyweight Title, but he nailed Undertaker with a low blow. The match was restarted by Teddy Long and Undertaker retained the World Heavyweight Championship with a Tombstone Piledriver.
4 The Undertaker & Big Show Vs. The Rock ‘n’ Sock Connection – SmackDown (9/9/99)
On the September 9, 1999, edition of SmackDown, The Undertaker and Big Show were looking to reclaim the WWE Tag Team Champions from The Rock ‘n’ Sock Connection. It wasn’t an ordinary Tag Team Championship match as they competed in the first-ever tag team Buried Alive match.
The Undertaker was far from 100% as he was suffering from a groin injury that would rule him out of action for the remainder of the year. This was an enthralling match, and Triple H interfered by clocking Big Show in the back with a sickening sledgehammer shot. Nonetheless, Undertaker and Show recaptured the WWE Tag Team Championship.
3 The Undertaker Vs. Mr. Kennedy – Armageddon 2006
Mr. Kennedy became one of the fastest rising stars in SmackDown history, and he defeated a plethora of World Champions. He even defeated The Undertaker in a First Blood match at Survivor Series 2006. The Demon of Death Valley was out for retribution, and he collided with Mr. Kennedy in a rematch at Armageddon in a Last Ride match.
The Undertaker and Kennedy battled at the top of the Armageddon structure. The Phenom took a bump with Kennedy pushing Undertaker off the structure. That should have seen Kennedy victorious, but Undertaker had a refusal to stay down. He regrouped, and he planted Kennedy with a Tombstone on the top of the hearse. Undertaker finished off with Kennedy with a Tombstone and drove him away in the hearse.
2 The Undertaker Vs. Faarooq – King Of The Ring 1997
Parts of Undertaker’s five-month run as WWE Champion was quite forgettable. That’s because of Shawn Michaels, Bret Hart, and Steve Austin. Nevertheless, at King of the Ring 1997, Undertaker put his WWE Championship on the line against Faarooq in the main event.
Faarooq was the leader of the Nation, and he was aiming to make history as the first Black man to win the WWE Championship. Paul Bearer was by Undertaker’s side as he was manipulating him, and would reveal a dark secret if he did not follow Bearer’s orders. Faarooq gave a good account of himself, but the result was never in doubt with Undertaker retaining the WWE Championship.
1 The Undertaker Vs. Steve Austin & Triple H – Insurrextion 2001
At Insurrextion 2001, The Undertaker faced off with WWE Tag Team Champions Steve Austin and Intercontinental Champion Triple H in a handicap match. There was a caveat as the Texas Rattlesnake’s WWE Championship was up for grabs. Although Undertaker had to pin Austin to win the WWE Championship.
This match is often forgotten about since it took place in the UK. Although three heavy hitters were involved, this clash is never spoken about. Undertaker prevailed, but he did not take home the WWE Title since he pinned the Texas Rattlesnake instead.