#4 Mr. McMahon - 56:38 (Royal Rumble 1999)
Vince McMahon's victory in the 1999 Royal Rumble Match, let alone his appearance in the match, is something that fans have not cherished a lot over the subsequent years.
After all, it was the peak of WWE's most famous period. There were plenty of more talented superstars in the match who could have benefitted a lot from the win, and McMahon didn't actually wrestle in the Main Event of WrestleMania 15. However, one can not take away the fact that The Boss had one of the longest stays in the match, not only by a winner, but by any performer in the Royal Rumble history.
Entering at number two, McMahon spent 56 minutes and 38 seconds in the Royal Rumble match, the same as the number one entrant Steve Austin, who was the last and only person eliminated by The Boss in the match. He spent most of the match outside the ring, mostly at the announcer's table, and was inside the ring only when he was getting beaten by Austin.
McMahon's victory made him the first superstar to win the Royal Rumble match with a solitary elimination to his name, a feat that was repeated by Randy Orton in 2017, and he had the second-longest stay in winning performances at that time.