In 1949, Ip Man, who has been suffering from chronic gastric pain, travels alone to Hong Kong. He starts by teaching Wing Chun on the rooftop of a building which houses a hotel staff's general association. He meets and accepts new students, including Tang Shing, Leung Sheung, Wong Tung, Lee King and Chan Sei-mui. During that period of time, Ip Man's wife, Cheung Wing-sing, also comes to Hong Kong to join her husband, but returns to Foshan shortly after because life in Hong Kong is hard. The couple never saw each other again because Cheung died not long after returning to Foshan. His son Ip Chun comes from Foshan to Hong Kong to join him.