5. Stephanie McMahon
http://www.youtube.com/watch?v=oh8pHI9jzn4 Believe it or not, but a match between Stephanie McMahon and Brock Lesnar was a thing that actually happened. It wasn't much of a contest admittedly, but Stephanie can claim a match with a former UFC Champion because of it. Stephanie later had a more (in)famous male vs. female encounter, an I Quit match no less, when she faced Vince at No Mercy 2003. Stephanie had had some wrestling experience, including a memorable match with Trish Stratus in 2001, but not much in-ring interaction with the guys (except the occasional Rock Bottom or Stunner). It was a somewhat disturbing match, with Vince getting the win after choking his own daughter with a lead pipe. The violence in it is the most gratuitous in a male vs. female match we've seen and is one that the internet seems to have forgotten (I couldn't find a video), and is one that WWE is probably glad you've might have forgotten too.