Hmmm, I might put Custer up there. Plenty of skirmishes with JEB that I believe, Custer won. Then again, how about Nathan Bedford Forrest?
Ping
Custer was audacious and aggressive. A hero in the press who got a lot of his men killed during the Civil War. A trait he repeated while finally getting himself killed too at the Little Big Horn.
Custer was talented but impetuous which led to his defeat at Little Big Horn. Custer typically got the best of Stuart - so as a cavalier you'd have to give the edge to Custer. IIRC, it was Custer who stopped Stuart's frantic attempt to rejoin Lee at Gettysburg in an action which may have ultimately determined the outcome of the Civil War.