While the WWE Chairman has taken a ton of executive and creative decisions backstage, he’s been involved in a lot of on-screen action as well. From being the babyface commentator on WWE programming to the conniving Mr. McMahon gimmick and beyond, the WWE head honcho has done it all.

Vince McMahon has even squared it out in the middle of the ring with some of the legends of WWE. Given his shrewd nature and the authority that he holds, Vince has even managed to beat some top Superstars in a match. Let us look at six such names who came second when facing Vince McMahon inside a WWE ring.

#6 Bobby Lashley

The breadcrumbs for this feud were laid down during the Battle of the Billionaires between Vince McMahon and Donald Trump. Both men chose a Superstar to represent them and the loser would have his head shaved off.

Vince McMahon chose Umaga while Trump chose Bobby Lashley. Lashley won the match at WrestleMania 23 with some help from guest referee Stone Cold Steve Austin.

One week prior though, Vince faced Lashley on RAW in a no disqualification match to teach him a lesson. The match saw interferences from Lance Cade, Trevor Murdoch, Chris Masters, John Morrison (then Johnny Nitro), and Umaga, but in the end, it was a low blow from Vince McMahon that sealed the deal.

Vince McMahon would also challenge for Lashley’s ECW World Heavyweight Championship at Backlash that year and the 3-on-1 handicap stipulation allowed the former to win the match. Vince dropped the title a month later to Lashley again.

#5 Stone Cold Steve Austin

Vince McMahon and Steve Austin feuded for the majority of the Attitude Era but the duo took their rivalry to a WWE ring only during the controversial angle involving the Ministry of Darkness.

Led by The Undertaker, the Ministry of Darkness kidnapped Stephanie McMahon twice. During the second instance, The Deadman tried to marry Stephanie but the latter was saved by Austin.

Vince McMahon was eventually revealed as the “Higher Power” controlling the merged The Corporation-Ministry of Darkness faction known as Corporate Ministry.

Vince’s McMahon’s wife Linda and Stephanie were so shocked that they transferred their 50% stake in WWE to Steve Austin. To gain back the control of the company, a handicap ladder match was set up with Vince and Shane McMahon going against Stone Cold Steve Austin at the 1999 King of the Ring PPV.

It was a brutal affair with Vince McMahon and Steve Austin going at each other. Eventually, while both men were down, Shane climbed the ladder to claim the briefcase and win the match for him and his father.

#4 Shawn Michaels

Vince McMahon’s feud with Shawn Michaels began when he decided to deal the latter the same hand as the one Bret Hart got back at Survivor Series 1997.

Mr. McMahon distracted HBK during the 2006 Royal Rumble match, which allowed Shane O’Mac to eliminate him from the match. It was later announced that Vince McMahon would be facing Michaels at WrestleMania 22.

During the March 6 episode of RAW, Shawn Michaels faced off against Shane McMahon and the latter ran victorious. Shane O’Mac then spoke to Lilian Garcia as she announced that HBK would be facing Vince McMahon next that very moment. As a numb Michaels lay on the mat, Vince pinned him to secure the win in merely six seconds.

Vince McMahon would later recreate the Montreal Screwjob at the Saturday Night’s Main Event XXXII during Shane and Michaels’ Street Fight with HBK bearing the brunt this time. The WWE Chairman would later go on to lose his No Holds Barred match at ‘Mania. Father and son would join forces again to get the better of Michaels at the Backlash PPV.

#3 Triple H

Triple H is the one Superstar whom Vince McMahon has beaten the most number of times in singles or handicap matches, four times to be exact. The first instance of this was during the match for the then WWF Championship on the 16 September 1999 episode of SmackDown. Stone Cold Steve Austin would interfere to help Mr. McMahon reign supreme and become the WWF Champion.

The next time HHH and Vince McMahon feuded was right after the latter’s altercations with Shawn Michaels as mentioned in the previous slide. The Game was ordered by the McMahons to beat up HBK but he refused and that eventually led to the reunion of D-Generation X.

Vince McMahon would have a No Holds Barred match against Triple H who was attacked backstage by Lance Cade & Trevor Murdoch and Shane McMahon backstage. The Game bled as he walked to the ring for the match and a few more interferences later, the WWE head honcho ran victorious.

The other two instances occurred during the infamous storyline of Hornswoggle being Vince McMahon’s illegitimate son. Triple H would make fun of Vince during the whole angle and as a result, the latter had matches with The Game on two consecutive weeks of RAW to teach him a lesson.

Firstly, Mr. McMahon would join hands with Carlito and beat Triple H in a Handicap Steel Cage match. The next week, Vince and The Game would face off in a traditional match with Carlito as the referee. During the match, Triple H would hit Carlito because of his bias towards Vince and the ref would disqualify him, thereby handing the WWE Chairman another win.

#2 Ric Flair

Following the end of the Monday Night Wars with WCW, where WWE ran victorious, Ric Flair made his return to Vince McMahon’s promotion in 2001.

Upon arrival, he was embroiled in a feud with Vince himself as The Nature Boy claimed to be the half owner of WWE. Shane and Stephanie McMahon had apparently sold their shares in order to purchase WCW and ECW and their stake was now owned by none other than Ric Flair himself.

An irate Vince McMahon booked a match between the two at Royal Rumble 2002 which Flair won. Eventually, Vince would control SmackDown while Ric Flair took over Monday Night RAW.

To decide who would have complete control over proceedings, Vince McMahon and Ric Flair took part in a No Holds Barred match on the 10 June 2002 episode of RAW.

The Nature Boy was busted open during the encounter but managed to lock in the Figure Four Leglock on Vince McMahon after a few back-and-forths. It was then that Brock Lesnar would interfere and deliver the F5 on Ric Flair. Vince would then get the pinfall and gain complete control of WWE.

#1 The Undertaker

Back in 2003, the world of pro wrestling was high on Brock Lesnar, and Vince McMahon was no different. The Beast had helped Mr. McMahon win back the 100% ownership of WWE against Ric Flair and at No Mercy 2003, the WWE head honcho decided to return the favor.

The Undertaker faced Brock Lesnar in a Biker Chain match for the WWE Championship where a chain was hung above the ring. If retrieved, it could be used as a weapon. Vince would interfere and prevent The Undertaker from getting his hands on the object. Brock capitalized, hit ‘Taker with the chain, and retained his title.

In the following episode of SmackDown, The Undertaker won a handicap match against Lesnar and Big Show which allowed him to pick an opponent for Survivor Series. He picked Vince McMahon and the stipulation was a Buried Alive match.

As expected, The Undertaker dominated the majority of the match and dragged Vince McMahon to the burial site. However, after a bit of retaliation and interference from Kane, the WWE Chairman was able to pick up the victory.

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