7. Shawn Michaels
Just like this best friend, the Heart Break kid has also won against the Deadman twice. Although, both of his wins came with the help of interference from Kane, Triple H, and Chyna.
6. Edge
The "R-rated" superstar cashed the money in the bank contract on the Undertaker. But in 2007-08, Edge handed the Undertaker a couple of defeats more.
5. Triple H
The "King of Kings" never managed to win against the Undertaker at WrestleMania but he has defeated the Deadman a number of times.
4. Mankind
We haven't seen something like Mick Foley's characters in WWE after he retired. Foley's three different characters were Dude Love, Cactus Jack and Mankind. And Mankind defeated the Deadman in the Boiler Room Brawl match for the first time.
3. Stone Cold Steve Austin
Arguably the most popular Wrestler of all time, Stone Cold Steve Austin has also got better off The Undertaker at times. Austin defeated the Deadman for the World title in SummerSlam 1998 for the first time.
2. Kane
Undertaker's brother Kane made his debut in 1997 and he quickly became the Furious rival of The Undertaker. Following the feud, the Big Red Machine defeated the Deadman in three consecutive pay-per-views.
1. Brock Lesnar
No other superstar on the list can take the place of Brock Lesnar. The Beast Incarnate defeated the Deadman in WrestleMania 30 and he broke Undertaker's winning streak of 21 straight wins on the biggest stage.