In 1950, the Wing Chun master Ip Man (played by Anthony Wong) moved to Macau with his wife Cheung Wing-ching (played by Yuen Qiu) and their son Ip Chun to make a living in Hong Kong. During a challenge, Leung Shuang (played by Hung Tin-ming) conceded defeat and became Ip Man's disciple. Subsequently, Ip Man took in several students, including Li Qiong (played by Jiang Luxia), Chen Simi (played by Gillian Chung), Deng Sheng (played by Chan Siu-Chun), Wang Dong (played by Chow Ding-Yu), and Wu Zan among others. However, the most noteworthy was his little-known relationship with his confidante Jenny (played by Zhou Chuchu). Wang Dong and Wu Zan were combative and often challenged other schools, frequently requiring Ip Man's mediation. One night, workers clashed with Leung Shuang on a rooftop during a meeting, and Ip Man intervened to subdue everyone. On the other hand, Deng Sheng was obsessed with fame and fortune, colluding with corrupt police officers. Ip Man enlightened Deng Sheng about righteousness, and eventually, Deng Sheng secretly helped release Li Qiong, who had been arrested due to a police-civilian conflict. In 1959, Kowloon Walled City was ruled by the local gang leader (played by Hung Hing-hing), engaging in nefarious activities. Deng Sheng agreed to secretly help Wei Batian (played by Luke Wan) win the lion dance competition, allowing the local leader to manipulate the outcome. On the day of the competition, Wei Batian ambushed Wu Zhong (played by Zeng Zhiwei), and Ip Man intervened to rescue Wu Zhong, defeating...