Probably Bruce Lee.
If they fought 10 times there would be 10 different outcomes. it's a stupid and pointless question that no one can possibly answer.
IP Man was Bruce Lee's teacher in Wing Chun. But I believe Jeet kun Do which his what Bruce lee's man style was could overpower Wing Chun anyday.
look up history of Ip man in found out yourself.. I do feel people always ask about bruce lee.. first no one here knows either person..
I just watched IP man 2 and I was wondering who would win if IP man at the prime of his life went in a fight against Bruce lee in the prime of his life because i was just wondering.
