When Ip Man and Ip Tin-chi (Ip-Man's adopted brother) were still young, their father persuaded Chan Wah-shun (Sammo Hung) to teach them Wing Chun so as they can defend themselves. Not long laterm Ip Man's father passes away and they stay at the martial arts centre with Chan Wah-shun and the rest of the practitioners. There, they befriend with Lee Mai- wai, who practices Wing Chun.
However, Chan Wah-shun's illness has become worse and his departure was too soon. Ip Man (To Yu-hang) and his brother, Ip Tin-chi (Fan Siu-Wong) continues to learn Wing Chun from their senior, Ng Chung-sok (Yuen Biao), before leaving Foshan to study in Hong Kong at St. Stephen's College.
In Hong Kong, Ip Man and his schoolmates are insulted by a racist British (Andy Taylor). Ip Man wants him to swallow his words, but the British continues to slur them in mandarin. Ip Man challenge the British to a duel and defeats him, and they become friends. Ip Man's popularity soar after the incident.
Ip Man meets Master Leung Bik (Ip Chun) while trying to buy medicine for his British friend. Leung Bik is the son of Master Leung Jan, Chan Wah- shun's teacher. Ip Man exchange blows and techniques with Leung Bik but was defeated and he learns a different, improved style of Wing Chun from Leung Bik to improve his skill. Meanwhile in Foshan, Ip Tin-chi rose to become a prominent businessman under another Wing Chun martial arts association.
Years later, Ip Man returns and reunites with his friends at the martial arts centre. His brother, Ip Tin-chi is excited to see him that the two exchange blows and Ip Tin-chi sees a different pattern that is different from the original Wing Chun. Ng Chung-sok, who was there saw Ip Man has mastered a new style of Wing Chun from Leung Bik, which differs from Chan Wah-shun's orthodox style. Ip Man is punished for learning a different style.
Soon, Ip Man falls in love with Cheung Wing-shing (Huang Yi), the daughter of the vice-mayor of Foshan, Cheung Ho-tin (Lam Suet). When Lee Mei-wai (Hins Cheung) found that Ip Man loves Cheung, she accepts Ip Tin-chi's love and marries him.
On their wedding night, her godfather is murdered and Ip Man is arrested as a prime suspect after being witnessed struggling with him. Cheung Wing-shing went to the police department and lied that Ip Man was with her the entire evening to have him released on bail. Lee Mei-wai discovers a letter to Ip Tin-chi, regarding the assassination of her godfather. She was saved by Ip Tin-chi when she attempted suicide and they tried to leave for Foshan but were caught by the Japanese authorities. The pregnant Lee Mei-wai is captured and Ip Tin-chi is forced to kill Ng Chung-sok because Lee Mei-wai showed the letter to him.
At the martial arts centre, Ng Chung-sok was defeated by Ip Tin-chi and Kitano Yumi (Bernice Liu). Ip Man arrives in time to save Ng Chung-sok from being killed and then defeat the Japanese and Ip Tin-chi. Ip Tin- chi reveals that he is actually a Japanese named Tanaka Eiketsu, who was sent to China from a very young age to work as an undercover agent. He performs seppuku to end his life.
Ip Man rushes off to the pier to rescue Lee Mei-wai. He defeats the Japanese mastermind and rescues her. At the pier, they discover that the Japanese have been smuggling Japanese children to China, possibly as future undercover agents, similar to Ip Tin-chi.
Ng Chung-sok is seen narrating the story of the night to new apprentices at the martial arts association. Ip Man's son, Ip Chun, is seen among the new apprentices. Ip Man arrives back at the association and is shown married to Cheung Wing-shing.
However, Chan Wah-shun's illness has become worse and his departure was too soon. Ip Man (To Yu-hang) and his brother, Ip Tin-chi (Fan Siu-Wong) continues to learn Wing Chun from their senior, Ng Chung-sok (Yuen Biao), before leaving Foshan to study in Hong Kong at St. Stephen's College.
In Hong Kong, Ip Man and his schoolmates are insulted by a racist British (Andy Taylor). Ip Man wants him to swallow his words, but the British continues to slur them in mandarin. Ip Man challenge the British to a duel and defeats him, and they become friends. Ip Man's popularity soar after the incident.
Ip Man meets Master Leung Bik (Ip Chun) while trying to buy medicine for his British friend. Leung Bik is the son of Master Leung Jan, Chan Wah- shun's teacher. Ip Man exchange blows and techniques with Leung Bik but was defeated and he learns a different, improved style of Wing Chun from Leung Bik to improve his skill. Meanwhile in Foshan, Ip Tin-chi rose to become a prominent businessman under another Wing Chun martial arts association.
Years later, Ip Man returns and reunites with his friends at the martial arts centre. His brother, Ip Tin-chi is excited to see him that the two exchange blows and Ip Tin-chi sees a different pattern that is different from the original Wing Chun. Ng Chung-sok, who was there saw Ip Man has mastered a new style of Wing Chun from Leung Bik, which differs from Chan Wah-shun's orthodox style. Ip Man is punished for learning a different style.
Soon, Ip Man falls in love with Cheung Wing-shing (Huang Yi), the daughter of the vice-mayor of Foshan, Cheung Ho-tin (Lam Suet). When Lee Mei-wai (Hins Cheung) found that Ip Man loves Cheung, she accepts Ip Tin-chi's love and marries him.
On their wedding night, her godfather is murdered and Ip Man is arrested as a prime suspect after being witnessed struggling with him. Cheung Wing-shing went to the police department and lied that Ip Man was with her the entire evening to have him released on bail. Lee Mei-wai discovers a letter to Ip Tin-chi, regarding the assassination of her godfather. She was saved by Ip Tin-chi when she attempted suicide and they tried to leave for Foshan but were caught by the Japanese authorities. The pregnant Lee Mei-wai is captured and Ip Tin-chi is forced to kill Ng Chung-sok because Lee Mei-wai showed the letter to him.
At the martial arts centre, Ng Chung-sok was defeated by Ip Tin-chi and Kitano Yumi (Bernice Liu). Ip Man arrives in time to save Ng Chung-sok from being killed and then defeat the Japanese and Ip Tin-chi. Ip Tin- chi reveals that he is actually a Japanese named Tanaka Eiketsu, who was sent to China from a very young age to work as an undercover agent. He performs seppuku to end his life.
Ip Man rushes off to the pier to rescue Lee Mei-wai. He defeats the Japanese mastermind and rescues her. At the pier, they discover that the Japanese have been smuggling Japanese children to China, possibly as future undercover agents, similar to Ip Tin-chi.
Ng Chung-sok is seen narrating the story of the night to new apprentices at the martial arts association. Ip Man's son, Ip Chun, is seen among the new apprentices. Ip Man arrives back at the association and is shown married to Cheung Wing-shing.