#2 Seth Rollins defeated Brock Lesnar twice in 2019
Seth Rollins' most memorable win in his WWE career came at WrestleMania 31 in 2015, when he cashed in his contract against Brock Lesnar and Roman Reigns. A few months prior to that win, Rollins had faced Lesnar and John Cena in a triple threat match at Royal Rumble, where Lesnar retained his title.
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Brock Lesnar then won back the title a few months later at Battleground to end the feud with Rollins.
The two Superstars then faced each other the next time in 2019, where Rollins won his first singles match against Brock Lesnar, at WrestleMania 35, to win the Universal Championship. Rollins, though, held the title for just three months as he lost the belt to Brock Lesnar at Extreme Rules.
Rollins ended the feud with Lesnar with another win against The Beast, this time at SummerSlam 2019. This win against Brock Lesnar made it two wins for Rollins against The Beast in 2019, which is a brilliant record to have against a dominant force like Lesnar.