During WWE’s famed “Attitude Era,” Shane McMahon had a number of memorable matches against a variety of opponents. Falling from great heights against The Big Show and Steve Blackman, trying to stop Test from marrying his sister, and brawling all over Texas with dad at WrestleMania. However, there is one match that McMahon is arguably best known for, and that match recently celebrated its 25th anniversary.
At WWE King of the Ring 2001, McMahon wrestled Kurt Angle in a Street Fight that has gone down as one of the most memorable, and most violent matches in company history. Both men were forever changed coming out of it, but they were also bonded for life due to what they put themselves through, and in light of the match now being a quarter of a century old, McMahon took to his social media pages to both celebrate the bout, and to jokingly tease that they should do it all again.
I Just got off the phone with Kurt where we reminisced about this match and how proud we both are of it and that it has withstood the test of time. Thank you all for supporting us both over these many years. You guys are the greatest fans in the world. https://t.co/0yyhMRcIic
— Shane McMahon (@shanemcmahon) June 25, 2026
Both men were extremely hurt coming out of the match, with McMahon sustaining a concussion and having several lacerations over his body due to being thrown through two panes of plexiglass. The infamous Suplexes through the glass were actually meant to be a lot simpler, but WWE staff ordered plexiglass instead of sugar glass, meaning that what McMahon and Angle were dealing with was very real. In the lead-up to that spot, Angle suffered a broken tailbone after taking a Suplex on the concrete floor, which Angle himself credits for not giving him the strength to Suplex McMahon through the glass the first time around.
The match is now remembered as one of the greatest spectacles in WWE history, and while Angle and McMahon were very proud of themselves, even high-fiving each other in wheelchairs at the hospital afterwards, Vince McMahon was furious with the bout. Vince was reportedly very close to coming out and stopping the match to avoid his son receiving any more damage, but was talked out of it and allowed the match to continue.
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