The Undertaker rose in prominence within the 1990s, earning himself a spot in the main event, though it wasn’t until the 2000s where his in-ring work really reached that next level. The gimmick and in-ring experience all came together to produce a sea of great matches throughout the decade.

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In truth, it is hard to even narrow it down to just his 10 matches, with him having so many good ones on offer. He had some terrific feuds during this period - some of which will show up here - and stole the show on several occasions, most often in title matches and main events but also in non-title action too.

10 The Undertaker Vs. Jeff Hardy, Raw 2002

This match is an infamous one, with it often being viewed as one of the more memorable Raw matches of all time. New to the singles scene Jeff Hardy rose up to challenge the Undisputed WWE Champion in a ladder match, and it was a blast.

Undertaker managed to play the more methodical heel, adapting his style to the ladder match format wonderfully (it was his first of this stipulation too). Hardy was a terrific underdog, and managed to turn the crown into a frenzy with some great false finishes.

9 Six-Man Hell In A Cell, Armageddon 2000

Steve Austin, The Rock, Kurt Angle, Rikishi, Triple H and of course The Undertaker all entered the Hell in a Cell structure at Armageddon 2000 in what was one of the most unique Cell matches ever.

It featured some good spots, classic Attitude Era style brawling, and star power through the roof. Notable moments included The Undertaker chokeslamming Rikishi from the top of the Cell, which was arguably the highlight of the match. This was a great WWE Championship main event.

8 The Undertaker Vs. Edge, One Night Stand 2008

The Undertaker and Edge feuded throughout 2007 and 2008, and at One Night Stand they met in a Tables, Ladders, and Chairs match for the vacant World Heavyweight Championship.

The Undertaker would try his best to fight off the numbers of La Familia, but the numbers game was too much, and he was pushed off a ladder and crashed through several tables outside the ring in a phenomenal spot. The whole match was brilliant.

7 Batista Vs. The Undertaker, WrestleMania 23

Batista and The Undertaker would battle several times throughout their rivalry, and even though some other matches had stipulations attached, this one was arguably the best. It was a basic singles match but wrestled at a great pace with a lot of physicality attached too.

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This was one of Batista’s best WrestleMania matches ever, and it kicked off a spree of hits for The Undertaker at the Showcase of the Immortals, with him stealing the show from WrestleMania 23 to 29 with back-to-back-to-back (and so on) classics.

6 Edge Vs. The Undertaker, WrestleMania 24

For the second year in a row, The Undertaker walked into WrestleMania and won the World Heavyweight Championship in a great match. Edge showed that he had done his homework coming in, providing ingenious counters to everything The Undertaker had to throw at him.

This led to a very fun dynamic for their main event bout in 2008 which delivered in a big way. In the end, The Undertaker had to go deep in his locker and pull out the Hell’s Gate submission, which finally got the job done.

5 The Undertaker Vs. Kurt Angle Vs. The Rock, Vengeance 2002

Three of the best of all time walked into the main event of Vengeance in 2002, and despite having three completely different styles, they meshed perfectly to have a tremendous match for the Undisputed WWE Championship.

There were some brilliant near falls in the final stretch, with each man being made to look strong no matter the ending result. In what was a smart move, the near falls were all broken up, so everyone’s finishing moves were protected well. Ultimately, it was The Rock who found a way to win.

4 The Undertaker Vs. Edge, SummerSlam 2008

The third match to be mentioned in the top 10 from the feud between The Undertaker and Edge was their final clash at SummerSlam 2008 where they finally closed the chapter on what was a legendary rivalry.

The clashed inside Hell in a Cell, showcasing just how fun and chaotic a PG Era style of a Cell match could be. It was a spot-fest in all the best ways, and was jam-packed with several strong moments. Undertaker emerged victorious, getting the last laugh in their feud.

3 Brock Lesnar Vs. The Undertaker, No Mercy 2002

In a complete contrast to the Edge Hell in a Cell match, this one with Brock Lesnar at No Mercy 2002 was an absolute war. The pair beat the hell out of one another in a match which saw limited weapons but a lot of blood, and a great use of the Cell, particularly when it came to Lesnar targeting Undertaker’s broken hand.

The rivalry between these two was great in the early 2000s, with Lesnar looking more and more like a major star.

2 Kurt Angle Vs. The Undertaker, No Way Out 2006

For nearly half an hour these two did battle for the World Heavyweight Championship in a match that was jam-packed full of psychology.

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Undertaker’s selling of his leg for instance was world class, and it led to a great story told throughout with Angle managing to ground his much larger opponent. Angle managed to escape with a win at the end, rolling up The Deadman for the victory.

1 The Undertaker Vs. Shawn Michaels, WrestleMania 25

The Undertaker’s greatest match of the 2000s and arguably his greatest match ever came when he and Shawn Michaels put on an all-time classic at WrestleMania.

This was beautifully wrestled, featuring huge moments, big moves, smooth counters, and an electric audience who played their part in making this a mega showcase between two legends.