10 Biggest Ever Heel Vs. Heel WWE Matches

9. Stephanie McMahon Vs. Trish Stratus - No Way Out 2001

Stephanie McMahon was the heel wife of Triple H in the storyline that led to their eventual real marriage a few years later. Trish Stratus started in WWE about a year before their big match in February 2001 at No Way Out. Trish's role at the time was that of the mistress of Vince McMahon, who was so mean as a heel that he was drugging his wife Linda so that she was in a comatose state. The reason the match took place was because Stephanie was mad that Trish was "more than friends" with Vince even though Stephanie was a heel just like Vince and Trish were. It was still a match that made sense from the story perspective because fans just wanted to see these two women go at it. Give the women a lot of credit for putting on an entertaining match too. Neither woman had much experience in the ring yet they were able to have a solid match for the ten minutes they were given. William Regal showed up to decide the finish by helping Trish at first and then changing his mind to give Stephanie the win after he nailed Trish with a neckbreaker. They both stayed heel after this with Stephanie remaining in that role for over a year after this while Trish turned face a few months later once the angle with Vince was over.