14. The Undertaker Defeats Kane In An Inferno Match (February 22, 1999)
Vince McMahon turned face due to the ongoing threat of The Undertaker and his powerful heel persona. As the story developed, Undertaker started to play more mind games with McMahon, hinting that he was interested in his daughter Stephanie. Upon defeating Kane in an Inferno Match on Raw, 'Taker set fire to a teddy bear that apparently belonged to Stephanie as a child. This caused Vince to break down in tears, seemingly helpless to stop the hell that The Ministry Of Darkness were bringing to his company.