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Over two decades after Vince McMahon turned heel, it's still amazing how this calm and composed babyface announcer turned into possibly the evilest villain in the history of this business. Bret Hart bashing Vince on an episode of Raw in 1997 kicked off this slow heel turn, and in a matter of months, Vince had become a full-fledged heel. He went on to compete in the squared circle, going on to actually win the Royal Rumble Match in 1999 by eliminating his arch-rival Stone Cold Steve Austin.
Over the past 20 years, Vince McMahon has competed in a string of matches, and has mostly been used as a villain who would get pinned by the hero in the end, to send the fans home happy. But there have been instances where Vince actually won matches against top Superstars. Here are six megastars Vince McMahon has pinned.
#6 Randy Orton
Back in 2009, Shawn Michaels and Triple H arranged a birthday party for Vince McMahon on the August 24 episode of Raw. The same episode saw DX and Vince take on The Legacy (Randy Orton, Ted Dibiase, and Cody Rhodes) in a 6-man tag-team match.
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The bout ended when John Cena came out and threw Orton inside the ring, hitting him with an Attitude Adjustment. Vince McMahon then pinned Orton to end the night on a high note.
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#5 Ric Flair
On the June 10, 2002 episode of Raw, Mr. McMahon faced Ric Flair in a No Holds Barred Match, for 100% ownership of Monday Night Raw. Flair got busted open during the match. During the closing moments, Flair locked in the Figure Four, as Arn Anderson watched Vince McMahon writhing in pain.
Suddenly, Brock Lesnar hit the ring, prompting Anderson to flee. He hit Flair with an F-5 and helped Vince defeat the Nature Boy.
#4 Shawn Michaels
Heading towards WrestleMania 22, Vince McMahon and his son Shane McMahon got into a feud with Shawn Michaels. The duo cost Michaels a shot at the top title at WrestleMania 22 during the Royal Rumble Match.
At WrestleMania 22, Shawn Michaels defeated Vince McMahon in a bloody brawl, but this wasn't the end of the feud. Soon after, Vince and Shane met Michaels and "God" in a Tag Team Match at the upcoming PPV, Backlash. The match saw interference from The Spirit Squad, and the group helped Vince steal a victory against The Heart Break Kid.
The ending to the match saw The Spirit Squad throw Michaels on a table, followed by McMahon comfortably pinning him to win the match for his team.
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#3 Triple H
Back in 1999, Triple H met Vince McMahon on an episode of SmackDown, and put his WWE title on the line. McMahon was out to fight for the honor of his family, and did everything in his power to put down The Game, but to no avail.
Suddenly, Stone Cold Steve Austin came out and chaos ensued. Austin hit Chyna and Triple H with Stunners and put Vince's body on an unconscious Triple H. Shane McMahon made the three count and Vince became WWE Champion in shocking fashion!
#2 John Cena
On the road to WrestleMania 26, Vince McMahon met John Cena in a Handicap Gauntlet Match, which saw several WWE Superstars assisting Vince in putting down Cena. Vladimir Kozlov, Drew McIntyre, Jack Swagger, Mark Henry (albeit reluctantly), and Batista all helped Vince to defeat Cena.
A thunderous Batista Bomb resulted in Vince pinning Cena with ease. Cena would go on to defeat Batista at 'Mania, while Vince would be destroyed by Bret Hart at the event.
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#1 The Rock
On the June 20th, 2000 episode of SmackDown, Vince McMahon teamed up with Triple H and Shane McMahon to take on The Rock, Undertaker, and Kane. The chaotic finish to the match saw a string of Superstars hitting the ring and launching a beatdown on the babyfaces. Edge, Christian, Test, X-Pac, Kurt Angle, A-Train, and many more assisted the villains in getting an upper hand over The Rock, Undertaker, and Kane.
In the end, Triple H hit a Pedigree on The Rock. This was followed by a Leap of Faith from Shane. Vince then hit The Rock with his own finishing move, The People's Elbow, which led to him pinning The Great One to a chorus of boos.
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