Under boxing rules? Average dude in any kind of shape is probably going to win, if he is not a pussy soy boy. Street fight? The trained speedy chick wins out because she gets to nail the guy in the nuts, throat, or kidneys. Boxing severely restrains the kinds of hits that would end normal fights. I say this as someone who bounced in their 20s and had to break shit up between ripped diesel dykes back in the day, and even they had a hard time hurting me (but I was actively training martial arts and not such a fat fuck at the time). The minute you let a trained person, especially if they are short and fast, hit someone in the nose or nards, that person is going to win, regardless of gender, over a less trained individual. But under the scope of boxing (and frankly a lot of softer martial arts sparring) rules, mass and bone density is pretty fucking impossible to overcome. The wiry carpet munchers pretty much went down from one solid hit center mass from me (only threw a punch because they went for the balls, honestly) and those were easily the toughest women, physically, I have ever met in real life. Unless you have taken a punch its hard to grasp how much the physics of the male mass advantage matters. Its why men in casual brawls avoid the nuts and throat, because we would kill someone if we didn't.
TLDR, boxing rules average dude who has been in a fight likely wins. Anything goes, money is on the trained fit chick.