And knowledge in wing chun-Ip Man is the leading artist as he was Bruce Lee's teacher. So if the fight was in Wing Chun only.....it's obvious who would prevail -maintaining the idea that both martial artists are in similar age/health/weight/height/speed/etc. However the interesting thought would be comparing Bruce Lee's own Martial Art Jeet Kun Do Vs. Wing Chun alone, could possibly lead different results. PS in response to a negative comment regarding the slapping in Wing Chun, the martial art was developed by female Chinese nuns- the idea of slapping is not to knock out or severely injure your opponent, it is to startle them, keep there minds occupied, and disorganized. Logic- if someone throws a heavy punch- yes it may knock u out- if it hits you but it takes more time - than multiple quick rapid slaps to the face. So if you miss that heavy punch your opponent has time to react and defend before the next heavy punch. But .... If you are being slapped in the face constantly without pause, how much time do u have to react properly??? Most people's defense is to bring up there guard or move away. That's good but A wing Chun expert would take advantage of u leaving your body open when guarding your head and vice versa and would never let u gain any distance to begin with. Hope u enjoy my post! Free knowledge! Stay curious!