Who takes it?
All hespect to helio, but the ip man is the ip man 
Let's even say 1933 - 20 year old Helio versus 40 year old Ip Man, if you want
Yip was hip,more aura...
Jiu Jitsu beats Kung Fu 9 out of 10 times
graciesrule - Jiu Jitsu beats Kung Fu 9 out of 10 timesWing Chun
Did Ip Man really fight anyone?
banco - Did Ip Man really fight anyone?I don't know too terribly much about him but supposedly he had a great many matches against anyone who challenged him, but always behind closed doors so that no one would have to be ashamed of their loss. As for the validity of that story, I couldn't say.
IP man was a drug addict...
true story (opium )
Sagawa or Ueshiba vs. Helio would be much more intersting.....
Helio all day.....
Internet protokoll man doesn't fuck around 
Helio via "Web-Whoopin"...
Ip man stands no chance. :)
RockTheVote -
internet protocal man cannot defend helios 50/50 guard. helio via 50/50 to twister roll to crackhead control to armbar from guard.
Helio is rolling in his grave at the mention of his name alongside 50/50 right now. Double entendre intentional.
Intenet Protocol man is funny shit
Intellectual Property Man has copyright on all the different techniques.
Leigh -Lol, anecdote from work. Software engineers in his fifties asks me if I've seen Ip Man. He watched it by accident thinking it was called I.P. Man (internet protocol man).
Lol! Same thing here. I work with some network engineers. We're always talking MMA and I brought up IP man, to which one of them said he had seen it accidentally because he thought it was Internet Protocal man, and thought it was going to be a Tron type movie.
I don't think anyone with Wing Chun as a base has ever fought credibly. There is no earthly reason to believe the head guy would be any better.
Match above is between the best guy in Germany and a famous teacher out of Hong Kong.
Helio would take him like it is his job.