Every Stone Cold & Vince McMahon Match, Ranked From Worst To Best
Daniel Foster
Updated on September 23, 2026
When it comes to WWE's long history of rivalries, feud between renegade wrestling star Stone Cold Steve Austin and WWE chairman Vince McMahon deserves a lot of praise. The rise of Austin as the new face of the company saw McMahon becoming the heel authority figure who was trying to stop said ascent. Many fans were vocal in expressing their disdain for Vince following the infamous Montreal Screwjob, but this actually inspired him to ramp up the heat he could generate.
RELATED: It's Me, Austin! The 10 Most Hilarious Vince McMahon Memes
Meanwhile, Austin’s popularity grew even stronger, with fans loving every single moment or match where he could make McMahon pay for his actions. The success of the angle caused Vince to have matches for the first time, with quite a few where he went face to face with Austin. Find out which ones stand out the most as we rank every Austin and McMahon match ever.
8 Steve Austin vs Vince McMahon (RAW: April 13, 1998)
The is the first match between Stone Cold and the boss man himself, though that's about all there is to this bout. At the time, McMahon was desperate to stop Austin’s success and challenged Austin to a match with his hands tied behind his back.
The match was ruled a no contest when Mick Foley entered the ring as Dude Love before any action started. Foley attacked Austin to start a feud for the WWE Championship. WWE booked the McMahon/Austin as a fake out for ratings. Moving forward, they learned from this mistake.
7 Steve Austin & Vince McMahon vs The Rock & D'Lo Brown (RAW: May 11, 1998)
One of the stranger matches featuring both Steve Austin and Vince McMahon saw them teaming up against Nation of Domination members The Rock and D’Lo Brown. Vince was still a heel and forced Austin to team with him in the match.
This was done in storyline to stack the odds against Austin and set him up. The finish was a no-contest when McMahon attacked Austin during his comeback. Mick Foley made his way to the ring to get the better of Austin ahead of their big PPV match, which was all (of course) orchestrated by Vince.
6 Steve Austin vs Vince & Shane McMahon (King of the Ring, 1999)
Vince McMahon teamed with his son Shane McMahon in a ladder match against Steve Austin at King of the Ring 1999. The ladder match was set up to decide who would get full control of the company moving forward.
RELATED: 10 Things You Learn About Stone Cold From His Book
It was a terrible match, though, with the McMahon duo struggling in the ring. A confusing ending saw a mystery figure raising the briefcase whenever Austin came close to winning as Vince and Shane stole the win.
5 Steve Austin, Vince McMahon & The Rock vs The Undertaker, Shane McMahon & Triple H (RAW: June 10, 1999)
RAW received a star-studded main event in June of 1999 with six huge names involved. Vince McMahon was now a face, teaming with Steve Austin and The Rock against the heel trio of The Undertaker, Triple H and Shane McMahon.
The match only lasted about five minutes, with the storytelling of three rivalries all playing out at the same time. Vince’s team pulled off the win as he celebrated victory with the two biggest stars of the Attitude Era.
4 The Corporation vs Steve Austin (RAW: February 8, 1999)
A special edition of Saturday night RAW featured the huge attraction of Steve Austin running a gauntlet against The Corporation. If Austin could get past everyone, he would have Vince McMahon the ring.
Things played out that way with Austin defeating Ken Shamrock, Test, Kane, Chyna and The Big Boss Man all via DQ. However, this was actually all part of The Corporation's plan to weaken Austin for the end, where Vince defeated him. It set up the huge singles match between Austin and McMahon at the following PPV.
3 Steve Austin & Vince McMahon vs Chris Jericho & Chris Benoit (Smackdown: June 5, 2001)
In 2001, a torn quad forced Triple H to end his tag team run with Steve Austin faster than expected. But a in a shocking turn of events, Vince McMahon replaced Triple H in a rematch for the WWE Tag Team Championship during an episode of SmackDown.
RELATED: 5 Things We Hated About Stone Cold Steve Austin As A Heel (& 5 Things We Loved)
The face team of Chris Jericho and Chris Benoit won to continue their momentum building towards a triple threat match with Austin. Vince barely got involved, but the three elite workers helped make it work.
2 Royal Rumble (1999)
The rivalry between Steve Austin and Vince McMahon reached a new level in the 1999 Royal Rumble. Austin and McMahon were the first two entrants in the eponymous match and ended up fighting all over the venue, with The Corporation helping Vince.
The end saw them back in the ring as the final two competitors. Austin was distracted by The Rock, which led to McMahon eliminating him for the shocking victory. The heat thrown at Vince was overwhelming, since the audience felt disgusted at Austin being cheated. This, however, worked wonders for the storyline.
1 Steve Austin vs Vince McMahon (In Your House 27: St. Valentine's Day Massacre)
Steve Austin and Vince McMahon’s rivalry peaked at In Your House 27: St. Valentine’s Day Massacre in a steel cage match. To ramp up the stakes, McMahon put the WWE Championship title shot that he won in the 1999 Royal Rumble on the line.
Austin did a great job carrying Vince and it may have been the best match of the boss’ career. The two delivered a remarkable brawl, with Big Show debuting at the end. Fans were stunned when Big Show came from under the ring and threw Austin into the cage. Unfortunately for Big Show and Vince, the force of the throw allowed Austin to win when the cage flew open and he touched the floor first.
