The year is 1959, where Ip Man lives in Hong Kong with his wife and his younger son. Trouble arises when a corrupt property developer and his thugs terrorize the school where Ip Man's son goes to. Ip Man and his disciples have to help the police guard the school day and night. On the other hand, Ip Man has to deal with his wife's terminal sickness, and at the same time faces a challenge from another Wing Chun fighter who ambitiously seeks to claim the Wing Chun Grandmaster title.

A Taiwanese girl named Bu has just been proposed to. While pondering the proposal, she finds a message in a bottle which inspires her go to Hong Kong to meet the guy, Albert, who wrote the message. However, she finds out that Albert is gay. A successful playboy businessman CN, and Howie have been rivals in love and business since school days. Howie finds out that CN is dating his girl and also trying to take over his company. Howie tells his guys to teach CN a lesson. Bu happens to be there and...