In 1950, Wing Chun grandmaster Yip Man (played by Anthony Wong) moved to Macau with his wife Zhang Yongcheng (played by Athena Chu) and their son Yip Chun, and later sought a living in Hong Kong. During a confrontation, Leung Siu (played by Bill Leung) admitted defeat and became Yip Man's disciple. Afterwards, Yip Man took on several students including Li Qiong (played by Jiang Luxia), Chan Sei Mei (played by Gillian Chung), Deng Sheng (played by Chan Siu-Chung), Wong Dong (played by Chau Ding-Yu), and Wu Zan. However, the most notable was his little-known relationship with his close friend Jenny (played by Zhou Chuchu). Wong Dong and Wu Zan were competitive and often engaged in confrontations with other schools, frequently requiring Yip Man's mediation. One night, workers clashed with Leung Siu during a rooftop meeting, and Yip Man intervened to subdue everyone. On another front, Deng Sheng was obsessed with fame and profit and colluded with corrupt police officers. Yip Man tried to enlighten Deng Sheng, who ultimately secretly assisted Li Qiong, who was arrested due to a clash between police and citizens, in getting released. In 1959, the Kowloon Walled City was under the control of the local thug Di Tou Long (played by Hung Hing), who was involved in illegal activities. Deng Sheng agreed to secretly assist Wei Ba Tian's (played by Luk Wai-Kong) lion dance team to win, allowing Di Tou Long to manipulate the outcome of the competition. On the day of the competition, Wei Ba Tian ambushed Wu Zhong (played by Eric Tsang), and Yip Man intervened to save Wu Zhong, defeating Wei Ba Tian. Yip Man and Wu Zhong became close friends.
