The following is a timeline of the WWE career of Vince McMahon. Listed is every PPV match (excluding battle royals in which he was not involved in the ending) and title change that he has been involved in. Bolded items represent title victories while italicized items represent title losses.
1999
1/24 Royal Rumble - Vince McMahon won the Royal Rumble match by last eliminating Steve Austin
2/14 St. Valentine's Day Massacre - Steel Cage Match: Steve Austin beat Vince McMahon
6/27 King of the Ring - Handicap Ladder Match to become CEO: Vince & Shane McMahon beat Steve Austin
9/16 SmackDown - beat Triple H to win the WWE Championship
9/20 RAW - vacated the title
12/12 Armageddon - Triple H beat Vince McMahon in a match where if Vince won Triple H would have to annul his marriage to Stephanie
2000
6/25 King of the Ring - Six-Man Tag Match for WWE Title: The Rock became champ by pinning Vince McMahon in a match featuring The Rock, Kane & The Undertaker battle Triple H, Vince & Shane McMahon
2001
4/1 WrestleMania X-7 - Street Fight: Shane McMahon beat Vince McMahon
2002
1/20 Royal Rumble - Street Fight: Ric Flair beat Vince McMahon
2003
3/30 WrestleMania XIX - Hulk Hogan beat Vince McMahon
7/27 Vengeance - Vince McMahon beat Zach Gowen
10/19 No Mercy - I Quit Match: Vince McMahon beat Stephanie McMahon. As a result, Stephanie lost her job as GM.
11/16 Survivor Series - Buried Alive Match: Vince McMahon beat The Undertaker
2006
4/2 WrestleMania 22 - No Holds Barred: Shawn Michaels beat Vince McMahon
4/30 Backlash - No Holds Barred Match: Vince & Shane McMahon beat Shawn Michaels
8/20 SummerSlam - D-Generation X beat Vince & Shane McMahon
9/17 Unforgiven - Hell in a Cell: Shawn Michaels and Triple H beat Vince McMahon, Shane McMahon, and the Big Show
2007
4/1 WrestleMania 23 - Donald Trump's Hair vs Mr. McMahon's Hair: Bobby Lashley beat Umaga. As a result, Vince McMahon lost his hair.
4/29 Backlash - 3-on-1 Handicap Match for the ECW Title: Vince McMahon, Shane McMahon, and Umaga beat Lashley. As a result, Vince McMahon is the new champion.
5/20 Judgment Day - 3-on-1 Handicap Match for the ECW Championship: Bobby Lashley beat ECW World Champion Vince McMahon, Shane McMahon, and Umaga. Since he did not pin Mr. McMahon, he did not win the title.
6/3 One Night Stand - Street Fight for the ECW Title: Lashley beat Vince McMahon to win the title
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