#2 (Tied) Triple H - 6 world title matches at WWE Royal Rumble
Just like the World Title scene at WrestleMania, Triple H was always in the World Title scene during the Royal Rumble season between 2000 and 2005. In fact, he either challenged or defended a World Title on all but one of the shows in that period, and we all know what he achieved in 2002.
The Game's journey began way back in 2000, with his highly acclaimed WWF Title defense against Cactus Jack in a Street Fight. He followed this with a loss to Kurt Angle the very next year.
Between 2003 and 2005, he had three successive World Heavyweight Title defenses at the Royal Rumble. It started with a victory over Scott Steiner in 2003 in a rather underwhelming match, and ended with another against Randy Orton in 2005.
Between these two successful defenses lies his brutal Last Man Standing encounter against Shawn Michaels, which ended without a clear winner.
He featured in his final World Title bout at the Royal Rumble in 2016, when he made a surprise return at #30 and won the WWE World Heavyweight Title for the 14th time in his career.