In 1950, Ip Man (Anthony Wong), the first generation master of Wing Chun school (played by Anita Yuen) and his wife Zhang Yongcheng (played by Anita Yuen) took their son Ye Zhun to live in Macau, and then went to Hong Kong to make a living. In a competition, Liang Shuang (played by Hong Tianming) was defeated and became Ip Man's teacher. Later, Ip Man successively accepted Li Qiong (played by Luxia Jiang), Chen Simei (played by Gillian Chung), Deng Sheng (played by Jordan Chan), Wang Dong (played by Zhou Dingyu), Wu Zan and others as disciples. But the most eye-catching thing is a little-known story with his confidante Jenny (played by Zhou Chuchu). Wang Dong and Wu Zan were aggressive and often "discussed" with other sects, often requiring Ip Man's mediation. One night, workers and Liang Shuang had a conflict at a rooftop meeting, and Ip Man took action to subdue them. On the other hand, Deng Sheng was obsessed with fame and fortune and colluded with corrupt police officers. Ip Man expressed his righteousness to Deng Sheng, and Deng Sheng finally secretly assisted Li Qiong, who was arrested for causing conflicts between the police and the people, to be released. In 1959, the Kowloon Walled City was led by the gangster Di Tou Lung (played by Xiong Xinxin) and engaged in bad activities. Deng Sheng agreed to secretly help Wei Batian (played by Lu Weiguang)'s Lions team win, so that the local dragon could control the outcome of the game. On the day of the competition, Wei Batian attacked Wu Zhong (Eric Tsang). Ip Man rescued Wu Zhong and defeated Wei Batian. Ip Man and Wu Zhong became sworn friends.
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