#4 Shinsuke Nakamura 2-1 (66%)

Shinsuke Nakamura’s first appearance at the Royal Rumble pay-per-view was back in 2018 when he made history by being the first wrestler to enter at #14 to win the Royal Rumble. At the same time, he also became the first wrestler since Alberto Del Rio in 2011, where their Royal Rumble match victory happened to be their debut match at the pay-per-view.
Whilst the King of Strong Style was unsuccessful in winning the WWE Championship at WrestleMania 34, he would still go on to win other Championships, including the United States Championship, where his second reign started at the Royal Rumble kick off show in 2019 against Rusev. However, despite his win, he would also get his first loss at the pay-per-view the same night when he entered the Royal Rumble match at #3 but was unable to win the Royal Rumble match twice in a row.
After confirming he’ll be in this year’s Men’s Royal Rumble pay-per-view, Nakamura will be looking to repeat the feat he did in 2017, and by the same token will extend his winning record at the pay-per-view.
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