The Undertaker is undoubtedly one of the greatest wrestlers of all time. He had a fantastic career, competing in WWE for three decades. In each of those decades The Undertaker had many unforgettable moments, but the 2000s were arguably the best decade for him.
In the 2000s, The Deadman won four Tag Team Titles, three World Heavyweight Titles and a Hardcore Title as well. In addition, The Undertaker delivered several outstanding matches throughout the years, including a handful of masterpieces.
10 2000: Six Way Hell In A Cell Match (Armageddon)
At Armageddon 2000, The Undertaker, Rikishi, Steve Austin, The Rock, Triple H and Kurt Angle battled in a Hell in a Cell match for the World Heavyweight Title. Obviously, the star power is huge in this match, making it impossible not to get invested in it. It was a chaotic brawl, absolutely brutal, violent and bloody, with mind-blowing spots like when The Undertaker threw Rikishi off the top of the cell. In the end, Kurt Angle was the man who prevailed to retain the belt.
9 2001: Vs. Triple H (WrestleMania 17)
WrestleMania 17 is a PPV for the ages, and one of the reasons is this tremendous match between The Undertaker and Triple H. Certainly this match wasn't as epic as the others at WrestleMania 27 and WrestleMania 28, but it was still a superb match, with hard-hitting action and some brutal spots. Maybe it was a bit overbooked, and it didn't make sense that the referee was knocked out for so long, but overall, it was fun to watch.
8 2002: Vs. Brock Lesnar (No Mercy)
On this occasion, The Undertaker challenged Brock Lesnar to a Hell in a Cell match for the WWE Heavyweight Title. This was another brutal and bloody match. Brock Lesnar showed that he is a true beast, defeating The Undertaker in epic fashion. Taker bled a lot, and Lesnar showed absolutely no mercy, yes, just as the PPV name reflects. Brock Lesnar and The Undertaker pushed each other to their limits and told a gripping story here.
7 2003: Vs. Kurt Angle (SmackDown)
On the September 4, 2003, episode of SmackDown, The Undertaker faced off against WWE Heavyweight Champion Kurt Angle. It was an excellent match in which both competitors fought with intensity from start to finish.
The Deadman showed great offense, looking like a pure striker, while Angle worked on Taker's leg with his impeccable technique, trying to keep him on the mat, where he was vulnerable. The storytelling was brilliant, and there were some top-notch counters and sequences. The bout ended in a no contest due to Brock Lesnar's interference.
6 2004: Vs. John Cena (SmackDown)
Surprisingly, in 2004, The Undertaker didn't have any truly amazing matches, and perhaps the only one somewhat outstanding was on the June 24 episode of SmackDown, when The Undertaker faced off against United States Champion John Cena in a non-title match. It was a 22-minute affair, with solid in-ring action and proper booking, as The Deadman got the win, but Cena looked great. Overall, it was an enjoyable bout.
5 2005: Vs. Randy Orton (WrestleMania 21)
In 2005, The Undertaker had an excellent trilogy of matches against Randy Orton, at WrestleMania 21, SummerSlam and Armageddon. All the matches were great, but the best was the first one at The Showcase of the Immortals.
Randy Orton's youth, rebelliousness and thirst for greatness against The Undertaker's experience, supernatural power and undefeated streak. It was a back-and-forth match, with amazing sequences and excellent work from both wrestlers. Orton stole the show, proving he was a natural heel and had a bright future, but in the end The Undertaker sent Orton to rest in peace.
4 2006: Vs. Kurt Angle (No Way Out)
At No Way Out 2006, The Undertaker faced off against World Heavyweight Champion Kurt Angle. This match turned out to be an all-time classic and one of the best matches of both men's careers. It was an extremely intense bout, with masterful in-ring psychology, perfectly executed maneuvers and amazing counters. Taker and Angle simply could not have told the story any better. Perhaps Angle's victory via roll-up wasn't a finish to everyone's liking, but that doesn't take away from the fact that this match was fantastic.
3 2007: Vs. Batista (Backlash)
In 2007, The Undertaker had a series of epic matches against Batista. They delivered a great match at Cyber Sunday, they collided in a formidable Hell in a Cell match at Survivor Series and had an outstanding match at WrestleMania 23, but their best match was at Backlash. The Undertaker defended the World Heavyweight Title in an impressive Last Man Standing match. Taker and Batista put body and soul on the line, and after 20 minutes of a tremendous battle, neither man could stand up and the match ended in a draw.
2 2008: Vs. Edge (SummerSlam)
This feud between The Undertaker and Edge was arguably the best in WWE that year. They delivered a masterpiece at WrestleMania 24, then collided in an amazing Tables, Ladders and Chairs match and finished things off in the main event of SummerSlam with a Hell in a Cell match. This match was absolutely phenomenal, with several mind-blowing spots and some call backs to complement perfect storytelling. Both men put each other through a hell of a lot of pain, and in the end, it was The Undertaker who prevailed.
1 2009: Vs. Shawn Michaels (WrestleMania 25)
At WrestleMania 25, The Undertaker went one-on-one against Shawn Michaels. This was not only Taker's best match of 2009 but arguably the best of his career, and that's saying something. Certainly, this match had a few minor flaws, like when The Undertaker nearly broke his neck on his ringside landing, but somehow that means Taker would actually do anything to win. We witnessed epic near falls, including one of the most incredible near falls in history, when HBK kicked out of the Tombstone Piledriver. In the end, The Undertaker emerged victorious from this legendary match.