Top 5 oldest Royal Rumble winners in WWE history 

#3 2016 Royal Rumble, Triple H - 46 years, 5 months, and 28 days

Triple H stood tall after the 2016 Royal Rumble

Another Evolution member to appear on this elite list is the 2-time Royal Rumble winner, Triple H. "The King of Kings" won his first Royal Rumble in 2002 after he entered at #22.

Fourteen years later, Triple H made his surprise return to the ring as the final entrant in the Royal Rumble Match. Roman Reigns defended his WWE World Heavyweight Championship against 29 other Superstars in that contest. To make things even more challenging for Reigns, Vince McMahon made him the first entrant.

#OnThisDay in 2016, @TripleH entered the Royal Rumble at number 30 to win the match & the #WWE ChampionshipThis was the first time the wwe championship was defended in a rumble match since 1992.#RoyalRumble #royalrumble2021 #hhh #tripleh pic.twitter.com/I36ON5M8We

— The Beermat (@TheBeermat) January 24, 2021

Before the pay-per-view, Reigns had brutally attacked Triple H. "The Game" avenged that beatdown by eliminating "The Big Dog" from the Royal Rumble. Triple H and Dean Ambrose were the last two Superstars left in the ring. The 46-year-old HHH tossed his rival out to the ringside area and secured the WWE World Heavyweight Championship.

The wrestler with the longest period between Royal Rumble wins is Triple H. He won in 2002 and again in 2016. pic.twitter.com/aZPcx89LtH

— Wrestling Stats (@WrestlingsFacts) January 27, 2019

Eventually, Triple H lost the title to Roman Reigns in the main event of WrestleMania 32. Still, "The Game" created a new record by being the oldest Superstar to win a Royal Rumble after entering in the final spot.