Madonna should win easy. Selena is tiny, a bigger young woman with size would give Madonna trouble. Still Madonna is in her early 50's and I imagine her body is more brittle than it was when she was in her 20's and 30's. Maybe Selena can get a lucky kick into Madonn'a knee damaging the joint then work on it with knee drops until Madonna can't put any weight on it. Selena then gets Madonna down and locks in a figure four until Madonna's knee pops, then she becomes easy pickins for the young cutie.
If that doesn't work then Selena's friend Taylor Swift interferes and although Madonna can take Taylor too, she can't handle both youngsters at once and the two youngbloods give Madonna her worse beating of her fghting career.