2. vs. Kane
Easily one of Shane McMahon’s toughest opponents ever, has to be the Undertaker’s (kayfabe) brother, “The Big Red Machine” Kane.
It was the summer of 2003 and Kane had just – for the first time ever – lost his mask permanently, which completely freaked him out.
After Kane attacked Sahne’s mother Linda McMahon and even tombstoned her on the stage, the game was on.
At WWE Unforgiven 2003 Kane defeated him in a Last Man Standing and 2 months later at WWE Survivor Series 2003, Kane defeated him yet again, this time in an Ambulance match.

