In the late 1950s, in Hong Kong which is under British colonial rule, Frank, a foreign property developer who colludes with the gangs and even the Police, is reclaiming houses and a school from the local community. It is not a good time for the Wing Chun master Ip Man to deal with young Bruce Lee who just applied for an apprenticeship. For the good of the people, he steps forward and re-enters the "battlefield". In collaboration with another Wing Chun practitioner Tin Chi, Ip Man rescues the children kidnapped by the gangs. Upon hearing the appreciation from the people, however, Ip Man encounters the biggest challenge in his life – his wife has got an incurable disease for a while! Besides, things go terribly wrong when Tin Chi starts to envy him, meanwhile Frank who turns out to be an extraordinary fighter takes revenge on him. Before the ultimate battle against Tin Chi, surprisingly, Ip Man accepts Bruce as an apprentice only if Bruce can teach him Cha-cha dance. Actually this tender-hearted husband intends to escape from battles and spend all his time taking care of his sick wife... Should he step up to defend his discipline of Wing Chun?