It’s January, you know what that means! Royal Rumble is almost here and wrestling fans are gearing up to kick off the Road to WrestleMania. The Royal Rumble match means a lot as the winner headlines WrestleMania. But over the years, there have been some questionable winners, including the 1999 Royal Rumble victory of WWE Chairman, Vince McMahon.

Vince McMahon wins the 1999 Royal Rumble

The Corporation storyline was in full swing, and Stone Cold Steve Austin couldn’t wait to get his hands on Mr. McMahon. Both men started the 1999 Royal Rumble match at #1 and #2, respectively. This was a rather bizarre yet entertaining Royal Rumble for a wrestling fan.

Austin went right after the WWE Chairman and hit him with repeated kicks to the chest in the corner. He followed with a stomp to his groin. It looked like Austin would throw McMahon out but decided otherwise as Golga entered at #3.

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As Austin turned his attention to Golga, Vince McMahon retreated from the ring. However, Austin soon followed him, fighting all over the arena from the stands to the halls and even toilets where Vince set Austin up for The Corporation to attack him.

The shenanigans from Vince McMahon didn’t stop there. He returned to the ring briefly before moving to commentary, leaving Ken Shamrock to clear the ring. Stone Cold wasn’t out for long either as he returned to the arena in an ambulance.

Stone Cold put down all the obstacles in his way from Ken Shamrock to Triple H and finally eliminated Big Boss Man with a stunner. Big Boss Man’s elimination meant Stone Cold and Vince McMahon were the final two men in the match.

Austin attacked Mr. McMahon, hit him with a chair, and got him back to the ring to deliver a Stone Cold Stunner. As Austin delivered the stunner, WWF Champion The Rock came down and talked trashed from ringside to Austin.

Just as The Rock climbed on the apron to taunt him, Stone Cold tried to attack him. This distraction allowed Mr. McMahon to sneak up on SCSA and throw him over the top rope to win the 1999 Royal Rumble match. Thios decision was heavily criticized by many.

Was Mr. McMahon’s victory necessary?

Honestly, it wasn’t. Yes, it did further the storyline between him and Austin for another PPV, but that’s that. We got Stone Cold vs The Rock despite the unfavorable odds. As per storyline, Mr. McMahon gave a $100,000 bounty to The Rock for helping him eliminate Stone Cold.

He then forfeited his WrestleMania title shot, so The Rock could have an opponent of his choosing. Then WWF Commissioner Shawn Michaels denied and ruled Stone Cold as the man who would face The Rock at WrestleMania XV because he was the runner-up in the Royal Rumble.

Yes, Vince McMahon winning the Royal Rumble sounds really weird, but it happened and it served a purpose. At the end, Stone Cold became an ever bigger star and eventually dethroned ‘The People’s Champ’ at WrestleMania XV.