Chuckie would not have stood a chance against Ip Man, who defeated many with Chuckie's style and skill, often more than one at a time ...
Only in Donnie Yen movies. In real life Yip Man was a good fighter in his prime, but not nearly as good as the movies portray, and he never fought anyone with Chuck’s skill level, or Chuck’s size. He wasn’t nearly as athletic as Bruce, who could fight as well as Yip’s best students (as demonstrated when he sparred with Wong Shun Leung during a visit to Hong Kong), and Chuck could hold his own against Bruce, though Bruce was better.