WWE Chairman Vince McMahon and his son Shane have been featured in many storylines over the years in WWE. The McMahons walk with a spring in their step as Vince is the owner and they can do nearly everything they want.
The McMahons are not great wrestlers by any stretch of the imagination, but they certainly know their way inside the squared circle. Unfortunately, there have been many cases of their egos getting the better of them at the expense of other competitors. They have had their fair share of defeats but in some matches they won, they should have been on the losing side.
10 Shane McMahon Vs. Roman Reigns - Super ShowDown 2019
Shane McMahon was known as the "Best in the World" after his last-minute exploits by winning the Best in the World Tournament at Crown Jewel 2018. Shane O'Mac had a chip on his shoulder but was once again a heel, which is a role he thrives in. Moreover, Shane went one-on-one with Roman Reigns at Super ShowDown 2019.
Shane did not come down the aisle alone as he had Drew McIntyre by his side, who Reigns beat at WrestleMania 35. It was a decent match and it was at the right length with Shane upsetting Reigns. He took advantage of McIntyre nailing Roman with a Claymore Kick when the referee was down but it was a match that Reigns should have had his hands raised as the victor.
9 Vince McMahon Vs. The Undertaker - Survivor Series 2003
At No Mercy 2003, The Undertaker was closing in on a fifth WWE Championship in a Biker Chain match with Brock Lesnar. However, the evil genius Vince McMahon made his presence felt by interfering and costing Undertaker the title.
Nonetheless, Undertaker and McMahon would meet at Survivor Series with The American Badass choosing the stipulation to be a Buried Alive match. As expected, Undertaker pummeled Vince and the chairman's face was a crimson mask. Big Evil carried McMahon to the gravesite but his brother Kane backstabbed him by aiding Vince to victory. Whilst, Undertaker should have won this match, it did mean that The Deadman would return at WrestleMania XX.
8 The McMahons & Umaga Vs. Bobby Lashley - Backlash 2007
Vince McMahon was humiliated at WrestleMania 23 as his representative Umaga lost to ECW Champion Bobby Lashley, who represented Donald Trump. It was The Battle of the Billionaires and the loser would have to get their head shaved bald.
Vince sported a durag to disguise his bald head. The chairman of the board ensured that he would get the last laugh at Backlash 2007 by taking out his frustrations on Lashley. Vince, Shane, and Umaga took on Lashley in a three-on-one handicap match with the ECW Championship at stake. The Samoan Bulldozer did most of the damage, and Vince pinned Lashley to capture the ECW Championship. Whilst, the result was shocking, it did not help the ECW Championship one bit.
7 Vince McMahon Vs. Triple H - SmackDown; September 16, 1999
The night after SummerSlam 1999, Triple H defeated Mankind to capture his first WWF Championship on Raw. However, whilst The Game was hoping for a long championship reign, that was not the case.
His future father-in-law Vince McMahon challenged him for the WWF Championship on an episode of SmackDown in September 1999. The Game loves to inflict pain on his opponents, and he decimated Vince, who was a bloody mess. Moreover, Stone Cold Steve Austin interfered and assaulted Triple H. Vince covered The Game and became the oldest WWF Champion at 54. It was a pointless title change, which did not need to happen and McMahon came to his senses by vacating the title on the following episode of Raw as he wasn't much of an active wrestler.
6 Shane McMahon Vs. Dolph Ziggler - Crown Jewel 2018
The WWE World Cup tournament was going through smoothly with plenty of former World Champions and rising stars from Raw and SmackDown participating. It was the second PPV event to be held in Saudi Arabia at Crown Jewel 2018. The final was supposed to pit Dolph Ziggler against The Miz.
However, Miz sustained a knee injury and was unable to compete. Therefore, SmackDown Commissioner Shane McMahon replaced Miz, and Shane O'Mac was not dressed for combat as he was sporting a pair of jeans. It was an embarrassment for the tournament with Shane winning, as Ziggler could have benefitted massively from being crowned "best in the world."
5 The McMahons Vs. Steve Austin - King Of The Ring 1999
Stone Cold Steve Austin was appointed as the new CEO of WWE as Linda McMahon stepped down from her duties and elected Austin to be her replacement. Vince announced that he and Shane would team up and square off against Stone Cold in a two-on-one handicap ladder match at King of the Ring 1999 with 100% ownership of WWE at stake.
Whilst, all three men aren't ladder match specialists, it was an entertaining affair. Austin was close to retrieving the briefcase suspended above the ring but an unknown figure would raise the briefcase higher and higher. Vince would fight Stone Cold at the top of the ladder but Shane sacrificed his father by pushing them both off the ladder. Shane clinched the briefcase, ensuring The McMahons were once again back in business.
4 Shane McMahon Vs. Shawn Michaels - Saturday Night's Main Event, March 18, 2006
For the first time in 14 years, WWE brought back Saturday Night's Main Event. Shane McMahon squared off with Shawn Michaels in the main event of the show in March 2006 in a Street Fight. HBK was scheduled to face Vince at WrestleMania 22 in a No Holds Barred match, and Vince was hoping for Shane to soften up HBK.
The Street Fight was an exceptional match with chair shots being taken. Moreover, Shane thrives in a Street Fight environment as he can use weapons. Once Shane locked HBK in the Sharpshooter, Vince recreated the Montreal Screwjob by ringing the bell, which allowed Shane to earn a huge win over Michaels.
3 Royal Rumble Match - Royal Rumble 1999
Vince McMahon did everything in his power to ensure that Austin would not compete for the WWF Championship again. However, his plans were thwarted as Stone Cold secured a spot in the 1999 Royal Rumble match after he defeated The Undertaker in a Buried Alive match at Rock Bottom: In Your House.
At the Royal Rumble, Stone Cold and Vince were the first two entrants. However, they spent large portions of the match outside of the ring which hurt the match. Nonetheless, the new WWF Champion The Rock distracted Austin, which allowed Vince to throw him over and win the Royal Rumble. Clearly, Vince was never going to headline WrestleMania XV, and it made sense for Stone Cold to win the Rumble.
2 Shane McMahon Vs. The Miz - WrestleMania 35
Shane McMahon and The Miz briefly held the Smackdown Tag Team Championship together, but Shane turned heel by backstabbing The Miz. The former partners settled the score at WrestleMania 35 in a Falls Count Anywhere match.
McMahon and Miz utilized their surroundings and took their battle into the crowd. Ultimately, they climbed up a scaffold and Miz performed a devastating suplex off it. Whilst both men were laid out, Shane managed to pick up a huge victory over Miz. Furthermore, The Miz should have been the victor as Shane O'Mac assaulted Miz's father, and a big win over a McMahon at a WrestleMania is a big deal.
1 The McMahons Vs. Shawn Michaels And "God" - Backlash 2006
"HBK" Shawn Michaels defeated Vince McMahon in their No Holds Barred match at WrestleMania 22, which was a sweet moment for HBK after suffering months of abuse from Vince. However, the evil genius once said, "He who laughs last, laughs loudest."
He wanted the last laugh and knew that HBK was now a Born-Again Christian. Therefore, at Backlash 2006, The McMahons took on Shawn Michaels and "God" in a tag team match. Technically, it was a No Holds Barred handicap match with The McMahons brutalizing Michaels in this encounter. Shane busted Shawn wide open with a devastating chair shot. Subsequently, they earned the victory with The Spirit Squad putting Michaels through a table with Vince getting his revenge by pinning Michaels.