10. Maria
http://www.youtube.com/watch?v=o799KiC5qfw Not satisfied with competing in just one match with a male wrestler, Maria has competed in two singles matches with men. It's not from her desire to break gender boundaries, because both matches were in fact attempts at punishing Maria. Her first was a match with Kurt Angle, for asking Eric Bischoff the wrong question during an interview, which she lost after being Angle Slammed. The second was a little mismatched, when she took on Umaga. Needless to say, she lost that too; but all credit to her for taking a Samoan Drop, and a Rikishi-style running butt to the face in the corner. Although they're more angles than matches, it's not every Diva who can say they've been in the ring with the likes of Umaga & Angle.