4. Triple H vs. Vince McMahon (Armageddon 1999)
Speaking of overbooking, that’s the perfect word to describe the wild No Holds Barred Match between Triple H and Vince McMahon from Armageddon 1999. On paper, this should definitely be last on our list, but for some insane reason, it was actually better than the aforementioned Austin/Undertaker Buried Alive Match.
Triple H and Vince McMahon fought all over the arena as the smoke and mirrors elevated the quality of their bout. Stephanie McMahon was the difference maker in the end, shockingly turning on her father to help The Game win their bout and forming the McMahon-Helmsley Regime that would rule the World Wrestling Federation in 2000.
On this day in 1999, Vince McMahon faced off against Triple H in the main event of Armageddon 99.
The match is most famous for Stephanie McMahon shocking the world and turning her back on Vince at the end of the match.
The birth of the McMahon-Helmsley Era pic.twitter.com/HgUbCkVJds
— NukemTalksWrestling (@NukemWrestling) December 12, 2023
