I think Bob Barker would win against Happy Gilmore in a real boxing match. It seems like he has more focus than Happy when it comes to golf, or sports. Happy is just too angry, and he ends up letting his anger get the best of him, especially when it comes to golf.
In the movie, Bob shot first with element of surprise, and easily over took Happy, in a real match, Happy would of easily over taken him due to major strength and bobs old age. I mean his drives are insane, and he can take a baseball to the chest without much pain. Obviously he would win.