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  • The Undertaker’s Best WWE Matches: From SmackDown 2003 to WrestleMania 23 That Defined an Era

The Undertaker’s Best WWE Matches: From SmackDown 2003 to WrestleMania 23 That Defined an Era

The Undertaker is mostly known for his heated matches in the WWE, which earned him the iconic title of the “Deadman.” He has one of the most iconic winning streaks, the WrestleMania streak. Undertaker also rose to fame due to his storyline with half-brother Kane and became the best tag team, ‘Brothers of Destruction.’ Take a look at her best WWE matches that still give fans goosebumps and nostalgic memories to 90s kids. 

Last Updated: August 20, 2025 | 3:24 PM IST
The Undertaker Vs. Steve Austin (Fully Loaded 1999)
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The Undertaker Vs. Steve Austin (Fully Loaded 1999)

The Undertaker feuded with Steve Austin in WWE Fully Loaded 1999. It was the first blood match for the WWE Championship. The stipulation of this match was massive if Austin lost, he would never get a title shot against Vince McMahon’s Corporation, and if Undertaker lost, Vince McMahon would be forced to leave the WWF forever. Steve Austin walked out as WWE Champion, marking it one of the most iconic First Blood matches.

The Undertaker Vs. Kurt Angle (SmackDown 2003)
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The Undertaker Vs. Kurt Angle (SmackDown 2003)

The Undertaker had a heated match with Kurt Angle on WWE SmackDown in 2003. The match was ended in a disqualification, but it was remembered as one of the best SmackDown matches. The Undertaker was the resulting winner.

The Undertaker Vs. Brock Lesnar (Hell In A Cell 2015)
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The Undertaker Vs. Brock Lesnar (Hell In A Cell 2015)

The Undertaker feuded with Brock Lesnar in WWE Hell in a Cell 2015. It was the final confrontation between them following their WrestleMania 30 (2014) when Brock broke The Undertaker’s 21-0 streak, and then at SummerSlam 2015, where The Undertaker defeated Brock. In a shocking finish, Brock F-5’d The Undertaker onto the exposed wood.

The Undertaker Vs. Batista (Backlash 2007)
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The Undertaker Vs. Batista (Backlash 2007)The Undertaker Vs. Batista (Backlash 2007)

The Undertaker feuded with Batista to win the World Heavyweight Championship at WWE Backlash 2007. It was a Last Man Standing match in which you can only win if you keep your opponent down for a 10-count. The match ended in a draw, giving it a shocking ending.

The Undertaker Vs. Batista (WrestleMania 23)
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The Undertaker Vs. Batista (WrestleMania 23)

The Undertaker won the Royal Rumble match in 2007, leading to his shot to fight against Batista at WrestleMania 23. The bout was full of intensity from the beginning which resulted in the win of Undertaker, marking it childhood best WrestleMania moment.

Disclaimer
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Disclaimer

This photo gallery is based on publicly available information, match records, and fan discussions related to WWE. All images, match clips, and trademarks belong to WWE and their respective owners. This content is created purely for entertainment and nostalgic purposes, with no intention of infringing on copyrights or intellectual property rights.