All 5 WWE Superstars who were the Royal Rumble Iron Men more than once

#3 Triple H (WWE Royal Rumble 1996 and 2009)

Triple H

One of the most accomplished Superstars in WWE and Royal Rumble history, Triple H's inclusion in this list isn't much of a surprise. He has won two of these matches and had many other impressive showings, the first of which came in 1996, back when he was Hunter Hearst Helmsley.

Triple H's Royal Rumble debut saw him last 48 minutes from the beginning. He had a much longer stay from number 1 a decade later, but Rey Mysterio topped that. Triple H lasted over an hour in the 2006 Rumble Match, only for Mysterio legend to eliminate him and win the match from number 2.

The Game did have another Iron Man performance at the Royal Rumble three years later, as he spent 50 minutes in the match from number 7. This might be his most valiant effort in Royal Rumble history, alongside his victory in 2002. Triple H eliminated six Superstars and reached the final two.

He had to contest with the entire Legacy trio - Cody Rhodes, Ted DiBiase Jr., and Randy Orton. Triple H eliminated Dibiase and Rhodes but was dumped out by Orton. He did win another Royal Rumble Match, coming away with the victory and the WWE Championship in 2016.