- In 1959, Ip Man (Donnie Yen) is settling into his low-profile life in Hong Kong. The film begins with Ip Man practicing his techniques on a wooden dummy, as a moth, foreshadowing the future, gently flutters and lands on the dummy.
The opening subtitles explain that his elder son, Ip Chun, has returned to Foshan to study, leaving him with his younger son Ip Ching and his wife Wing-sing.
A young Bruce Lee visits Ip and asks to become one of his students. After demonstrating his speed to Ip, Ip neither accepts nor rejects him and tells him to "come back later". Ip Ching is seen fighting with another boy, Cheung Fung, at school, and both boys end up with minor injuries. Wing-sing, along with Ip, is asked by Miss Wong, the boys' teacher, to come to the school. As an apology, the Ip family invite Cheung Fung to their home for dinner. At Ip's house, Cheung Fung displays rudimentary yet impressive Wing Chun skills. When Ip asks the boy who his mentor is, he says that it is his father, Cheung Tin-chi. Cheung shows up to pick up his son shortly after.