In 1950, Wing Chun master Ip Man (Anthony Wong) and his wife Cheung Wing Shing (Anita Yuen) brought their son Ip Chun to live in Macau, and then to Hong Kong to make a living. In a contest, Leung Sheung (Timmy Hung) was defeated and became Ip Man's apprentice. Afterwards, Ip Man successively accepted Li Qiong (Luxia Jiang), Chen Simei (Gillian Chung), Deng Sheng (Jordan Chan), Wang Dong (Zhou Dingyu), Wu Zan and others as his apprentices. But the most eye-catching is a little-known story with his confidante Jenny (Chow Chu Chu). Wang Dong and Wu Zan are aggressive and "talk hands" with other schools everywhere, and Ip Man often needs to mediate. One night, the workers and Leung Sheung had a conflict at a meeting on the rooftop, and Ip Man subdued them. On the other hand, Deng Sheng was obsessed with fame and fortune and colluded with corrupt police officers. Ip Man explained the righteousness to Deng Sheng, and Deng Sheng finally secretly helped Li Qiong, who was arrested for causing a conflict between police and citizens, to be released. In 1959, the Kowloon Walled City was led by a gangster named Di Tou Long (played by Xiong Yan Yan), who was engaged in illegal activities. Deng Sheng agreed to secretly help Wei Ba Tian's (played by Lu Weiguang) lion team win so that Di Tou Long could control the results of the game. On the day of the game, Wei Ba Tian attacked Wu Zhong (played by Zeng Zhiwei), and Ip Man rescued Wu Zhong and defeated Wei Ba Tian. Ip Man and Wu Zhong became close friends.