Triple H – 1:00:16 (2006)
The 2006 Royal Rumble was a special one in that it actually had two men break the one-hour mark. One of those men was Triple H, who barely edged out Flair’s time and nearly went wire-to-wire as the No. 1 entry that year.
He fought his way into the final three men with Rey Mysterio and Randy Orton, but a joint effort with Orton backfired, and Triple H was eliminated by Mysterio. Triple H may not have won that battle, but he has two Rumble wins to his credit, most recently in 2016 to win his 14th world championship.
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