Yip Man was the first martial arts master to teach the Chinese martial art of Wing Chun openly. He had several students who later became martial arts teachers in their own right, including Bruce Lee.
Yip Man was the last Wing Chun student of Chan Wah-shun when he was 70 years old, from 1903 till 1906 or 1906 till 1909. He was the second son of a very wealthy family in Foshan, Guangdong, and received an exceptional traditional Chinese education.
When Yip Man was thirteen years old he started learning Wing Chun. Because of his sifu's old age, Yip Man learned most of his lessons from his second sihing Ng Chung-sok. After three years Chan Wah-shun died, but one of his dying wishes was to ask Ng to continue with Yip's training.
At age sixteen, Yip Man went to attend school at St. Stephen's College in Hong Kong, which was an upmarket secondary school for wealthy families and foreigners who lived in Hong Kong.
According to one story, one day one of his classmates challenged him to try his martial arts skill with an older man. The man beat him with a few strikes. It turned out that the old man was his sibak Leung Bik (梁璧), son of his sigung. After that encounter, Yip Man continued to learn from Leung Bik from about 1908 till 1912 when Leung Bik died. At age 24, Yip Man returned to Foshan, and his Wing Chun skills had improved tremendously while he had been away. His fellow students believed he learned a different kind of martial art and treated him as a traitor to Wing Chun.
In Foshan, Yip Man didn't formally run a Wing Chun school, but taught Wing Chun to several children of his friends and relatives. Amongst those informal students, Chow Kwong-yue (周光裕 (六仔)), Kwok Fu (郭富), Lun Kai (倫佳), Chan Chi-sun (陳志新) and Lui Ying (呂應) were the most well known. Chow Kwong-yue was said to be the best student among his group of pupils, but he eventually went into commerce and dropped out of martial art all together. Kwok Fu and Lun Kai went on to teach students of their own and the Wing Chun in the Foshan and Guangdong area was mainly descended from those individuals. Chan Chi-sun died young, and Lui Ying went to Hong Kong; neither of them taking on any students.
During the Japanese occupation of China, Yip Man refused several invitations to train the Japanese troops. Instead, he returned to Hong Kong and opened a martial arts school. When he initially began the school, business was poor because his students typically stayed for only a couple of months before leaving. He was 5'2"-5'4" tall and weighed about 110-120 pounds and despite that, he was able to beat Leung Sheung (who was a master in Dragon Style and Choy Li Fut) who was 5'10" and 210 pounds in a friendly match. Thereafter Leung Sheung became Yip Man's first Hong Kong student.
Yip Man moved his school to Hoi Tan Street (海壇街) in Sham Shui Po and then to Lee Tat Street (利達街) in Yau Ma Tei. By that time some of his students were trained to a sufficiently high enough skill level that they were able to start their own schools.
Some of Yip Man's students and descendants compared their skills with other martial artists in combat. Their victories over other martial artists helped to bolster Yip Man's reputation as a teacher.
In 1967, Yip Man and some of his students established the Hong Kong Ving Tsun Athletic Association (香港詠春拳體育會).
Bruce Lee, Yip Man's most famous pupil, studied under him from 1954 to 1957. When Yip Man retired, many of his students were themselves teaching Wing Chun, including Leung Sheung, Lok Yiu, Wong Shun Leung, Tsui Shun Tin, William Cheung, Lo Man Kam (Yip Man's nephew), Moy Yat and his two sons Yip Chun and Yip Ching.
In 1972, Yip Man suffered from throat cancer and subsequently died on December 2 of that year. As a fitting obituary for the man, within the three decades of his career in Hong Kong, he established a training system for Wing Chun and Wing Tsun that eventually spread across the world.Sources: NewHaven Wing Chun