Continuing from where the first film left off, Wing Chun master Ip Man and his family move to Hong Kong in the early 1950s after their escape from the Japanese. Ip Man decides to open a school to teach Wing Chun and propagate the martial art, as well as make his living. However, as Ip Man's fame is not well known in the region, he has a hard time looking for students. After more than a week, a young man named Wong Leung (Huang Xiaoming) appears and asks to be taught Wing Chun. Upon first meeting the unassuming Ip, Wong challenges him to a fight and declares he will take him as his master and pay his school fees if he loses. After a couple of rounds of sparring, Ip easily defeats Wong, sending the humiliated young man leaving and coming back with a group of his friends who attempt to gang up on Ip. However, they are no match for Ip as he beats them. Stunned and impressed by his skills, Wong and his friends become his students. Eventually, Wong brings in additional students.One day, while Ip is out shopping for his family, he encounters his old friend Chow Ching-chuen (Simon Yam), who has become a beggar. Ip meets his son Kong-yiu, who tells him that his father suffered brain damage from a gunshot wound to the head while fleeing from the Japanese during their occupation years ago. As a result, Chow no longer recognises anyone.
Ip is saddened by his friend's fate and offers to help Kong-yiu take care of his father. He also helps Kong-yiu by finding him a job in a newspaper agency run by Leung Kan (Pierre Ngo), who earlier helped Ip find a suitable location for his Wing Chun school.


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