Vince McMahon Top 10 Best Matches – You’re Fired!

Vince was never famous for his in-ring ability, but he was apart of some fun matches. Here are his ten best.

Vincent Kennedy McMahon was never known for being a supremely talented technician nor an all-time great brawler in the ring, but there was always something about his matches that made them stand out.

Today, we look at the 10 best matches of the Genetic Jackhammer‘s in-ring career, including famous encounters like the St. Valentine’s Day Massacre 1999 Steel Cage showdown against Steve Austin, the infamous father vs. son affair against his own son, Shane O’ Mac, the 20-years-in-the-making marquee bout against the Hulkster, and much more. Let’s get into it!


10) Royal Rumble Match – WWF Royal Rumble, Jan. 24th 1999

IMG credit: WWE

The rivalry between Steve Austin and Vinnie Mac was at an all-time high amidst the Attitude Era. Austin wanted his shot at the WWF Championship by winning the Royal Rumble, but Vince wasn’t going to give him that. Instead, Vince hosted a Rumble number draw for Austin and “randomly” picked out a #1 on him while he drew a #30 for himself. However, then WWF Commissioner Shawn Michaels overrode said decision, placing Vince at a #2 spot and booked a ‘Corporate Rumble’ match where a guaranteed #30 spot would be on the line. That was ultimately won by Chyna after Austin caused a distraction on McMahon.

While it’s arguable one shouldn’t put a battle royale-style bout in a list of a wrestler’s best matches, Vince’s involvement in this one made it impossible to ignore. All of his interactions with Stone Cold in this match, from him getting brutalized by Austin, to him using his men to stop the Bionic Redneck, to that last shot of him actually eliminating Austin himself – it all made for tremendous entertainment. We all know this Rumble wasn’t the best theoretically, but those bits with Austin and Vince kept it at an enjoyable level, at least to some.

9) W/ Shane McMahon Vs. DX – WWE SummerSlam, Aug. 20th 2006

IMG credit: WWE & @LetsGoBackToWCW (Twitter)

The DX/McMahons feud primarily ate up most of 2006, so expect a lot of matches from that program to come up here! This was just after Triple H recently turned face by coming to the aid of Shawn, reforming DX in the process. In the weeks after, DX humiliated the McMahons in various fashions, making fun of them as the crowd laughed, much to the chagrin of Vince and Shane. This eventually led to a match between the two pairing.


The McMahons wisely weakened DX before the match by sending in the Spirit Squad, the 2006’s Midcard of Evil (Regal, Finlay, Kennedy), and the Big Show to attack them first. This set Shawn as the legal man for the team while HHH laid down on the floor. The highlight of the match came in the form of Vince and Shane doing old-school double-team maneuvers on Shawn, including the Hart Attack, Demolition Decapitation, and Doomsday Device. We got a couple of Attitude Era-like run-ins in the end before DX expectedly won via HHH’s Pedigree. A fun formula tag with additional sports entertainment values from the McMahons.

8) Vs. Bobby Lashley (ECW World Title, Street Fight) – WWE One Night Stand: Extreme Rules, Jun. 3rd 2007

IMG credit: WWE &

After getting screwed out of his ECW World Championship by Vince and company at Backlash 2007, Lashley was on the quest to regain the title back. This resulted in a series of PPV matchups between the two, where Vince would always book himself in a match that offered him situational advantages over Lashley, and he’d end up retaining the belt thanks to an underhanded technicality. The same applied for this one, as Umaga and Shane were both present for this Street Fight, ready to gang up on Bobby at any second.

Lashley dived at Umaga on the floor immediately, but he missed by about a foot, contacting him only with his feet. This soon became a glorified handicap match, with Lashley being mostly outnumbered by Vince & Co. It was dull at times, as Bobby was still too green to compellingly fight from underneath, but Vince’s hysterical schtick made it somewhat enjoyable at points. Lashley’s comeback was well-built, well-timed, and got the desired reaction needed. He pounded the living hell out of Vince with a steel chair and eventually got rid of Umaga and Shane after a few tries, before finally finishing with a Spear to reclaim the ECW Title.

7) W/ Shane McMahon & Big Show Vs. DX (Hell in a Cell) – WWE Unforgiven, Sep. 17th 2006

IMG credit: WWE

The DX/McMahons saga had finally reached its boiling point here. Weeks and weeks of humiliation and embarrassment finally caused the chairman to snap, as he hired his new acquaintance, the Big Show, to help him and his son combat the joke-cranking, degenerating duo from the late ’90s. In addition to being a handicap match, McMahon himself made the bout into a Hell in a Cell as well, looking to extinguish Shawn and Hunter once and for all.

This is considered to be arguably the most polarizing Hell in a Cell match of all time. I’m more inclined to the positive side, though not by a wide margin. Everyone bled like a stuck pig here, and they all took some nasty shots. Vince might just be the best overall worker in this one, thanks to his over-the-top expressions and villainous zany alone. DX won the blow-off of this infamous storyline by shoving Vince’s face into Big Show’s full moon and smashing a sledgehammer to the back of his head. One of the most absurd images you’ll ever see in wrestling, period. This whole thing was ridiculous from start to finish, and you’ll either hate it or love it.

6) Vs. Stone Cold Steve Austin (Steel Cage) – WWF St. Valentine’s Day Massacre: In Your House, Feb. 14th 1999

IMG credit: WWE & WhatCulture

After winning the 1999 edition of the Royal Rumble by last eliminating Stone Cold Steve Austin, Vince McMahon decided to forfeit his title shot, stating he wasn’t a full-time wrestler. There was a catch, however – should the winner forfeit the opportunity, the runner-up would take his place instead. Seeing this, the Chairman went back on his word and challenged Austin inside a steel cage at February’s In Your House PPV instead, with the #1 Contender for the WWF Title at WrestleMania XV hanging on the line.

This was about what you’d expect when you see Austin and Vince together: Vince getting his ass beaten up all over the place by Stone Cold. Vince took one hell of a beating at the hands of Steve, including a mammoth-sized bump on the Spanish announce table and one hella bladejob. The Giant Paul Wight from WCW popped up under the ring to help his new boss, but he made the mistake of throwing Austin into the cage, sending him out to the floor, thus giving him the victory instead. A smart finish that put over Show’s strength and gave fans a feel-good finish. This was all smoke and mirrors, but the crowd loved every moment of it.

5) Vs. Ric Flair (Street Fight) – WWF Royal Rumble, Jan. 20th 2002

IMG credit: WWE & EssentiallySports

After buying half of the WWF’s stocks using his business ploy, Ric Flair made a surprise return to the Federation on the RAW after Survivor Series 2001, shocking McMahon and the entire audience. He then used his power as the co-owner of the WWF to book Vince in a Street Fight against himself at the Rumble. This is Flair’s first match in nearly a full year, so there was doubts he would be able to pull out a good performance this late into his career.


With that said, this ended up being one of the best matches of the whole show. I honestly could see an argument for this being Flair’s best match in years. The start was only so-so to me, but it got a lot better once they did the brawling on the floor. Vince was the man in this match, managing to look hilarious and serious at the same time. They built to Flair’s comeback exceptionally well, and him kicking McMahon’s ass in the homestretch had me cheering along in excitement. Vince ate the loss in total McMahon fashion and gave Flair his best performance in ages. Call me crazy, but this was awesome.

4) Vs. Shawn Michaels (No Holds Barred) – WWE WrestleMania 22, Apr. 2nd 2006

IMG credit: WWE & Cultaholic

This feud had been teased in January 2006, and reached its new peak after Vince, along with his son Shane, screwed Shawn out of the Royal Rumble match. The father & son duo continued interfering in all of Shawn’s matches, and this eventually led to a WrestleMania clash between him and Vince. On the 32nd edition of Saturday Night’s Main Event, Shane defeated Shawn in a street fight thanks to another fishy WWE attempt at the Montreal Screwjob. Later on RAW, a No Holds Barred stipulation was announced for the match-up.

Seeing Vince McMahon getting beaten up will always guarantee entertainment. But seeing him get beat up for over 75% of the match? That’s even more entertaining! Though you could paint this as being an alleged handicap match and you wouldn’t be wrong, Shawn having to overcome all the odds made for a textbook wrestling story to follow. Vince took all of HBK’s moves like a boss (no pun intended), and this might be his best performance ever. Shawn taking his long-ass time setting up all the furniture in the final minutes might be too long for some, but that giant elbow drop off the ladder was worth it.

3) w/ Shane McMahon Vs. Shawn Michaels & “God” (No Holds Barred) – WWE Backlash, Apr. 30th 2006

IMG credit: WWE

Vince is still not done with Shawn after he was humiliated by him at WrestleMania, so on the RAW after the aforementioned show, he declared Shawn’s victory to be merely “an act of god”. He challenged Shawn to a No Holds Barred tag match at Backlash, where he would team with his son, Shane, while The Heartbreak Kid would partner with “God” (yeah…). The build-up to this highly controversial yet amusing matchup saw Vince McMahon doing backstage skits where he mocked God, even coming up with his own religion at one point, “McMahonisms”.

I thought this was tremendously wacky and entertaining in the most fun way possible. This crazed maniac version of Vince was the freaking best. The hilariously demonic facials, the ridiculous stunts, the funky music? Just priceless. Shawn and Shane took some mad bumps in this one, and they definitely carried the workrate portion of the match. Shawn’s initial shine and comeback were straight fire. The Spirit Squad made a late run-in, and they helped the McMahons outnumber HBK, launching him through a table and allowing Vince to get the pin. The screwjob finish isn’t my cup of tea, but it worked well under the context they were telling here.


2) Vs. Shane McMahon (Street Fight) – WWF WrestleMania X-Seven, Apr. 1st 2001

IMG credit: WWE

The storyline leading up to this featured some of the most ridiculous stuff ever seen in wrestling. From Vince making out with Trish Stratus in front of his immovable wife to Vince forcing Trish to bark like a dog on national TV to Shane buying WCW to get back at his dad… this was WWF soap opera at its highest peak. Mick Foley was your special guest referee for this one as a result of a storyline from late 2000 that saw Mick being stripped of his commissionership by Vince.

The first third of this wasn’t anything special – just them doing the usual Attitude Era brawl and throwing average offense in. It wasn’t until Stephanie came out to help her father avoid Shane’s big elbow that this officially kicked into high gear. Trish brought out the handicapped Linda to the ring, and she got into a catfight with Steph after pulling a double-cross on Vince. Vince put Linda in the ring and forced her to watch him beat up her own son, but she stood up and ultimately kicked him in the grapefruits for a goosebump-worthy pop! Mick Foley finally getting his hands on Vince and Shane hitting the Coast-to-Coast on his dad were both tremendously satisfying conclusions to this story. Sports entertainment at its absolute finest, this.


1) Vs. Hulk Hogan (Street Fight) – WWE WrestleMania XIX, Mar. 30th 2003

IMG credit: WWE

The WWE billed this as a 20-years-in-the-making encounter. And even though that might be stretching it out too far, it made the match that much more exciting on paper. The contract signing these two had on SmackDown featured Vince using Hogan’s own blood to sign the paper! Interestingly enough, this was actually advertised as the REAL main event of WrestleMania XIX at first, which is probably the REAL reason why this edition of ‘Mania didn’t do so good in terms of buyrate.

Notwithstanding the unimpressive buyrate however, these two went out there, gave us a classic story of good vs. evil told in a form of a bloody and messy brawl, and absolutely overdelivered under the low expectations. You have Vince dropping the big leg on Hogan through the announce table, long-time Spanish announcer Hugo Savinovich getting busted open after being hit with a chair shot, and THAT Crimson Mask shot of Vince while he rose up from the apron. This was nuts! Hulk Hogan made an amazing comeback towards the end and dropped three big legs on Vince to claim the victory and keep Hulkamania alive. Both men bled buckets and gave their all for this all-senior citizen Street Fight, and it resulted in one of the biggest highlights of that year’s Show of Shows. Unsurprisingly, this stood out as being Vince McMahon’s best match of all time.

And that’s gonna be it for today. Thank you so much for reading, and make sure to stay in touch in order for you to know about my next piece on the blog. Until then, have a nice day!