10 Things WWE Fans Should Know About The Undertaker Vs. Vince McMahon Rivalry

From 1990 to 2020, The Undertaker was one of the longest-enduring icons in WWE history, enjoying runs as both hero and villain as well as stints as a supernatural cowboy mortician and a totally normal biker. While he had noted rivalries with Steve Austin, Triple H, and Shawn Michaels along with a host of others, he also had one with WWE’s now-former boss, Vince McMahon.

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Starting once Vince McMahon became an official on-screen character in WWE — not just a play-by-play commentator — McMahon and The Undertaker had two feuds against one another and a handful of matches to go with them. Let’s take a look at their rivalry, including their final bout.

10 Originally Aligned Against Steve Austin

Before Vince McMahon and The Undertaker were enemies, they were actually allies in WWE’s World Title scene.

In his quest to take the WWE Championship off of his most hated enemy, Stone Cold Steve Austin, McMahon set up a match at Breakdown: In Your House in 1998 with the deck stacked against Austin: not only was it a triple threat with Kane and The Undertaker, but the match only ended when Austin was pinned. In the aftermath, ‘Taker and Kane ended up turning on McMahon, breaking his legs with the ring steps.

9 Attempted To Take Over WWE From McMahon

When 1999 began, The Undertaker embarked on a new version of his supernatural persona, a satanic cult leader who ended up gathering a group of midcarders and kayfabe vampires to form a new heel stable called The Ministry of Darkness.

Besides embracing evil and bringing out the dark sides of his various underlings, The Undertaker aspired to take over WWE and remake it in his image, thus making him a direct rival of not only Vince McMahon, but his Corporation faction.

8 McMahon Believed The Undertaker Was Going Overboard With The Gimmick

Blurring the lines of kayfabe and reality, Vince McMahon (the on-screen character) felt that The Undertaker was going overboard with his gimmick and actually believed the persona he was portraying. To deal with the ever-increasing threat of The Undertaker, McMahon relied on Kane — ‘Taker’s kayfabe brother — to deal with The Deadman.

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The Undertaker successfully defeated Kane in an Inferno Match, and from there The Ministry continued to harass Vince McMahon. Notable incidents included burning the childhood teddy bear of Vince McMahon’s daughter Stephanie, and erecting a flaming Undertaker-styled crucifix in Vince’s yard.

7 The Ministry of Darkness Kidnapped Stephanie McMahon

The above-mentioned teddy bear was a clear signal to Vince McMahon that Stephanie was going to be The Undertaker’s target in order to antagonize the elder McMahon.

Not only did the Ministry abduct Stephanie McMahon and brand her forehead with the Undertaker symbol, but they also subjected her to a “Black Wedding,” a sacrificial ceremony where Stephanie was tied to a large Undertaker crucifix. However, it would be Vince McMahon’s enemy Steve Austin who made the save for Stephanie.

6 McMahon Opposed The Merged Corporate Ministry

Around the time of the Black Wedding, Shane McMahon kicked his father Vince out of The Corporation and merged with The Undertaker’s group to form a mega-heel group called The Corporate Ministry. In response, a now-babyface group of ex-Corporation members — Mankind, Ken Shamrock, Big Show, and Test — formed an opposition group called The Union.

While the group didn’t last very long due to injuries and evolving WWE storylines, they found an ally in Vince McMahon, who sided with them in taking on The Corporate Ministry.

5 Their First Matches Were In 1999

Before Vince McMahon was revealed as The Higher Power secretly leading the Corporate Ministry, he joined WWE’s other top babyfaces in opposing The Corporate Ministry, leading to his first matches against The Undertaker. His first was on a May 1999 episode of Raw in which he teamed up with The Rock and Steve Austin against The Undertaker, Shane McMahon, and Triple H.

Weeks later — after Undertaker won the WWE Title at Over The Edge — brought the first singles match between McMahon and ‘Taker, a two-minute affair that ended in a disqualification thanks to The Undertaker attacking a ref.

4 Undertaker Opposed The McMahon-Helmsley Faction

One year after their first matches together, The Undertaker and Vince McMahon were once again in opposition, albeit with new alignments. In May 2000, The Undertaker returned from an eight-month layoff, shedding the supernatural trappings to become a biker nicknamed “American Badass.”

Meanwhile, a new authoritative heel group formed as Triple H married Stephanie McMahon, resulting in the creation of the McMahon-Helmsley Faction. With The Undertaker feuding with Triple H, Vince McMahon became The Deadman’s enemy once again.

3 Helped Defend Triple H’s WWE Championship From The Undertaker At King Of The Ring 2000

In The Undertaker’s pursuit of Triple H’s WWE Championship, Vince McMahon wasn’t just an ally of Triple H — he also competed in a match to ensure that his new son-in-law retained the belt. It was at King of the Ring 2000 that The Undertaker teamed with Kane and The Rock to challenge Triple H for the title, with Vince and Shane McMahon on Trips’ team.

While Triple H didn’t retain, The Undertaker didn’t win the belt either. Rather, it was The Rock who emerged as champion by getting a pinfall on Vince McMahon.

2 Renewed Their Rivalry In 2003

It was in 2003 that The Undertaker and Vince McMahon had another major run-in. At October’s No Mercy, ‘Taker took on Brock Lesnar in a Biker Chain Match for Lesnar’s WWE Championship, during which McMahon came out to interfere by pushing The Undertaker off of the top rope, allowing Lesnar to take advantage for the win.

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In the aftermath, Undertaker defeated Lesnar and The Big Show in a handicap match that stipulated that he could challenge anyone he wanted and chose Vince McMahon.

1 Vince McMahon Won Their Last Match

On top of choosing Vince McMahon as his opponent, The Undertaker also chose the stipulation of their bout: a Buried Alive Match at Survivor Series 2003. Over the course of the 12-minute bout, The Undertaker dominated McMahon, going as far as putting the WWE boss in the grave.

Before the actual burial could happen, however, Kane intervened in the match, throwing ‘Taker into the grave to assist in a Vince McMahon victory. The Undertaker took time off following this loss, returning to take on Kane at WrestleMania 20.