Yip Man would watch Chan Wah Shun drill his disciples in the ways of Wing Chun. Soon the boy’s visits became more regular until, Yip Man was about nine years old he approached Chan and asked to be accepted as a student. Chan Wah Shun was about 60 years old at the time and didn’t want to accept another disciple this late in life.
To discourage him, Chan told Yip that he would admit him as a student as soon as he could pay the tuition price of three taels of silver. But when Yip Man returned the next day with 300 pieces of silver, which was his entire life savings. So once Chan and Yip Man’s parents saw that this boy had such a strong desire to learn Wing Chun, his parents agreed to let him study. And Chan Wah Shun accepted him at which point, Yip Man became the last of Chan’s 16 disciples.
Yip Man studied with Chan Wah Shun for four years, until the old master’s death. Yip subsequently spent another two and a half years training with his senior, Ng Chung So. When Yip was 16 years old, his parents sent him to Hong Kong to attend St. Stephen’s College. There, he quickly fell in with a clique of classmates who liked to offer and accept kung fu challenges. He welcomed the opportunity to put his Wing Chun training to the real test.
Yip discovered that he liked to fight. He would accept a challenge on the slightest provocation. On one such occasion, a classmate named Lai dared Yip to go after an old kung fu practitioner who worked at the silk company of Lai’s father. The man was well into his 50s and very eccentric, but Lai insisted the man’s kung fu was very good.
That evening Yip Man found the man living on a fishing boat anchored near the typhoon breakers in Hong Kong Bay. Yip first performed the entire Siu Lim Tao form of Wing Chun. After that the old man agreed to a match. Yip promptly attacked the old man and quickly found himself in Hong Kong Bay. After repeated attempts and repeated soakings, Yip Man wanted to learn from the old man. Yip Man soon found out that the old man was Leung Bik. Leung Bik explained the difference in his Wing Chun compared to Chan Wah Shun’s and proceeded to take Yip Man as a student. Yip Man studied with Leung Bik for two and a half years.
Yip Man returned to Fatshan and told his seniors about the old man that he had met. When his seniors scoffed at him, Yip Man challenged them and defeated them with his newfound knowledge. Yip Man stayed in Fatshan where he was involved with the police and raised a family. In 1948 Yip Man fled to Hong Kong during the People’s Movement.
In Hong Kong, a homeless and penniless Yip Man was given refuge at a restaurant. Yip Man watched the instructor(Leung Sheung) there conduct a kung fu class. Leung Sheung at the time was a practitioner of Bak Mei and Dragon kung Fu. After watching the class for a time, Yip Man demonstrated his skill to Leung Sheung and Leung Sheung promptly became Yip Man’s first student in Hong Kong. After this Yip Man started teaching Wing Chun to the Restaurant Worker’s Association. Yip Man eventually moved his place of instruction.Yip Man trained excellent fighters, chief among them are Wong Shun Leung, Grandmaster William Cheung, and Bruce Lee. After 20+ years of teaching in Hong Kong, Yip Man passed away in 1972.