2. In the same age
That's like asking who would win, a martial artist or the guy that taught him martial arts? Probably the teacher.
Bruce Lee knew more martial arts than Ip Man who only knew of Wing Chun.
People always get confused by saying "Ip Man wins as he taught Bruce Lee". I disagree because Batman beat Ra's Al Ghul. LOL!
Bruce Lee
Chuck Norris
we both knew, master yip man taught bruce lee wing cun, before lee went to US and found JKD.
There's really no way to tell, so why bother asking?
1. In their peak
2. In the same age