As a child, Ip Man learns Wing Chun from Chan Wah-shun together with his adopted brother Ip Tin-chi and their mutual friend Lee Mei-wai, who later develops unrequited feelings for Ip while Tin-chi develops unrequited feelings for Mei-wai. After Chan's death from an illness, Ip Man continues to learn Wing Chun from his senior, Ng Chung-sok, before eventually leaving Foshan to study in Hong Kong.
In Hong Kong, after a field hockey match, Ip and his schoolmates are racially insulted by a Westerner, which Ip takes offence to. When the Westerner slurs them in Chinese, a further incensed Ip challenges him to a fight and proceeds to defeat him soundly. Following the incident, Ip's notoriety and popularity skyrocket. While getting medicine to treat the Westerner, who he now refers to as a friend, he meets master Leung Bik, who is actually the son of Leung Jan, Chan Wah-shun's teacher. Over the course of his time in Hong Kong, Ip Man learns a more varied and improved style of Wing Chun from Bik that differs greatly from Chan Wah-shun's orthodox style, and his martial arts prowess improves tremendously. Meanwhile, in Foshan, Ip Tin-chi rises to become a prominent businessman under another Wing Chun martial arts association, and Japanese businessmen arrive in Hong Kong.
Ip returns to Foshan after five years away and reunites with his peers. Believing that Ip has disrespected the memory of Chan Wah-shun by deviating from traditional Wing Chun techniques, an angry Chung-sok attacks him; not wishing to hurt his senior, Ip deliberately loses their fight, and their relationship becomes greatly strained as a result. Ip also later falls in love with Cheung Wing-sing, the daughter of the vice-mayor of Foshan. When Mei-wai realises that Ip Man loves Cheung, she accepts Ip Tin-chi's love for her. On their wedding night, her godfather is murdered and Ip is arrested as a prime suspect after being witnessed struggling with him; Cheung lies that Ip was with her the entire evening in order to have him released from jail. Mei-wai later discovers a letter to Tin-chi, revealing his involvement in the murder of her godfather, and informs Chung-sok. Attempting suicide, she is saved by Tin-chi, and they try to leave Foshan but are stopped by the Japanese. Mei-wai is captured and Tin-chi is ordered to kill Ng Chung-sok due to his knowledge of the letter; they also threaten to kill Mei-wai to ensure Tin-chi's co-operation.
At the martial arts association, Ng Chung-sok is defeated by Ip Tin-chi and the Japanese. Ip arrives in time to save Ng Chung-sok from being killed and then subsequently defeats the Japanese and Tin-chi. Tin-chi then reveals that he is actually a Japanese sergeant named Tanaka Eiketsu, and that was sent to China to infiltrate and work as an undercover agent. Ip then rushes off to the pier to rescue Lee. He defeats the Japanese and rescues Mei-wai, who tearfully reveals that she has miscarried Tin-chi's child; meanwhile, Tin-chi performs seppuku to end his life. At the pier, they discover that the Japanese have been smuggling Japanese children to China, possibly as future undercover agents, similar to Tin-chi.
Ng Chung-sok is seen narrating the story of the night to new apprentices at the martial arts association. Ip's son, Ip Chun, is seen among the new apprentices. Ip Man arrives back at the association and is shown married to Cheung.
Andy Taylor as foreign challenger at the field hockey match
Controversy
Sin Kwok-lam (Ip Man's son's student and producer) apologized and served tea to Yuen Jo Tong for misrepresenting his grandfather Yuen Kay Shan's reputation and status in Wing Chun history. (In the movie, Yuen Kay Shan was portrayed as Ip Man's younger kung fu brother, not as skillful as Ip Man). This had the Yuen and Yiu families criticize the movie in interviews. After the Yuen and Yiu families voiced their displeasure about Yuen Kay Shan's portrayal in the movie on Ip Man, movie producer Si Kwok Lam and co-producer Ip Chun apologized six times and "served tea" to Yuen Kay San's grandson, Yuen Jo Tong, for misrepresenting, and being disrespectful to, the legendary 1000 death duel champion during the 1920-1950s, Yuen Kay Shan.[3][4]
