10 Biggest Ever Heel Vs. Heel WWE Matches

By John Canton /

3. Kurt Angle Vs. Triple H - Royal Rumble 2001

The Stephanie McMahon vs. Trish Stratus match that was mentioned earlier happened because of what took place during this match. At the time, Angle was the heel WWE Champion that had become friends with Stratus, who was still fairly new at the time. Triple H was also a heel after a year of dominating the title scene with his then storyline wife Stephanie McMahon. It made sense as a WWE Title match at a major PPV like the Royal Rumble because they were two top guys who didn't like eachother. Plus there were storylines from the previous summer where it looked like Angle had a crush on Stephanie and she might have liked him too. It was a very good rivalry although they really didn't have the kind of blowoff match to end things that people were expecting. The match had an interesting dynamic since both guys were heels. There were all kinds of crazy things happening with the women fighting at ringside, Vince McMahon breaking it up because Trish was his sidepiece at the time and then Steve Austin factoring into the finish with an attack on Triple H, which gave Angle the fluke win. They had a lot of good matches together. This was one of their better ones even with both guys riding the heel side of the fence.