At the end of the 1950s, finally settled into a stable life, during his daily trip to take his young son to and from school, Ip Man meets another father Cheung Tin-chi; it so happens that Cheung is a fellow Wing Chun practitioner. Through their infrequent contact, the two fathers develop an interesting relationship. Unexpectedly, gangsters led by Sang are trying to take over properties in the neighbourhood and Ip Man decides to lead his students to guard the neighbourhood!

Ip Man's conflict with the gangsters becomes heated and he discovers that the boss behind the takeover is the foreigner Frank. Because Frank colludes with an English police superintendent, even the police inspector Fat Ball cannot do much to help. Undeterred, Ip Man stays to guard the Unexpectedly, Sang abducts the elementary school students to threaten the community and both Ip Man and Tin-chi's sons are taken. Ip Man arrives in time, and with Tin-chi's help, the Wing Chun duo save the children successfully! The gangsters' misdeeds are exposed in the media and the takeover of the neighbourhood ends. Unfortunately, tragedy hits Ip Man's family and he realizes that even though he is successful in saving the neighbourhood, he has neglected his own family. He decides to stay with his wife full time and leave other matters behind; troubles, however, do not leave him alone. Frank sends the Muay Thai Champion to attack Ip Man, disrupting his time with his family and threatens even his wife's safety. Ip Man is forced to confront Frank. After a fierce fight between Chinese and Western fighting styles, Ip Man earns Frank's respect!

Troubles keep coming. Tin-chi openly challenges Ip Man's authority and tries to make a name for himself by claiming to be 'authentic Wing Chun.' He openly challenges Ip Man into a fight! Between career and family, Ip Man chooses the latter and fulfils his promise to dance with Wing-sing. He gives up his reputation and status to be a real man.

Finally, with the encouragement from and arrangement by his wife, for himself and his family, Ip Man fights with Tin-Chi. Through this fight, he lets Tin-chi know that life belongs to oneself but not only to oneself. When Tin-chi is chasing after his ideals, he is effecting the life of his son. Like Ip Man, his life belongs to himself, to Wing-sing, to his sons and even to the martial arts.

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