Kiddo wins. While I think DD is pretty skilled in his show, and his pain tolerance and ability to fight through near fatal wounds is an advantage, the bride is just more skilled and has fought (arguably) deadlier opponents and won.
Kill Bill is a little wanked around here. Daredevil has fought superhuman ninja and beat people out of his weight class h2h. Kiddo doesn’t have feats of that type so Matt definitely has some advantages.