Chan Wa Soon was Yip Man's first teacher. Unfortunately Chan Wa Soon died at a young age and Yip Man did not finish his instruction. As a young man, Yip Man studied English at the St. Steven's Catholic School in Hong Kong. It was during this time that Yip Man met Leung Bik who was the son of Leung Jon. Yip Man challenged Leung Bik and was beaten. When Yip Man found out who Leung Bik was, Yip Man asked to become one of Leung Bik's students. Leung Bik, being a small man, did not use muscles. His style was not as hard as that of Chan Wa Soon. Yip Man was able to learn both the hard and soft elements.

After Yip Man's schooling in Hong Kong, he went back to China, his home town, worked as a policeman and trained cops in China. While working as a policeman, Yip Man killed someone in the line of duty. Fearing reprisals from the Communist government, he had to escape China and lost all his possessions. When he got to Hong Kong he only had his skills in Wing Chun with which to make a living. In Hong Kong Yip Man met his old time best friend Chung Choui (Go Dai Chung). Go Dai Chung was a Hung Sang Choy Lay Fut teacher and taught through the Chinese Restaurant Association - East and West. Teaching at both locales was too much for Go Dai Chung and he gave one to Yip Man which is located at Dai Lum Gai in Kowloon, Hong Kong so he could teach Wing Chun to make his living.

Leung Sheung was a bookkeeper for the Chinese Restaurant Association and an assistant teacher to Go Dai Chung. Leung Sheung challenged Yip Man and was defeated. Leung Sheung thereupon became Yip Man's first student. First generation students that never openly taught include Lau Ming, Lau Kau and Lee Yu. Other first generation students include Wong Shung Lueng, Choi Shung Tin, Lok Yu.Yip Man is known as the person who brought Wing Chun out of China.