Ip Man was born as Ip Kai-man (葉繼問) to Ip Oi-dor (葉靄多) and Ng Shui (吳瑞) as the third of four children. He grew up in a wealthy family in Foshan (Fatshan), Guangdong (Kwangtung), and received traditional Chinese education, alongside his elder brother Ip Kai-gak (葉繼格), elder sister Ip Wan-mei (葉允媚), and younger sister Ip Wan-hum (葉允堪).[3]
Ip started learning Wing Chun from Chan Wah-shun when he was 9[4] or 13.[5][6] Chan was 57 at the time, and Ip became Chan's 16th and last student.[7][8] Due to Chan's age, he was able to train Ip for only three years before suffering a mild stroke in 1909 and retiring to his village. Ip learned most of his skills and techniques from Chan's second-most senior student, Ng Chung-sok (吳仲素).[9]
At the age of 16, with help from his relative, Leung Fut-ting, Ip moved to Hong Kong and there he attended school at St. Stephen's College, by then a secondary school for wealthy families and foreigners living in Hong Kong.[3] Six months after moving to Hong Kong, a classmate of Ip's named Lai told him that a friend of Lai's father who was an expert in Kung Fu techniques was living with them, and had offered to have a friendly sparring match with Ip.[10]
At the time, Ip was undefeated so he eagerly accepted the challenge. He went to Lai's house on a Sunday afternoon and, after exchanging brief pleasantries, challenged the man to a duel. The man was Leung Bik and he easily overwhelmed Ip Man. Incredulous at the speed with which he had been countered, Ip requested a second duel and was beaten again, just as soundly.[10]
Discouraged by his defeat, Ip left without a word and afterwards was so depressed that he did not dare mention that he knew Kung Fu. A week later, Lai told him that the man he had fought was asking after him. Ip replied that he was too embarrassed to return, at which point Lai told him that Leung Bik had highly praised his Kung Fu techniques and that he was the son of Leung Jan, who trained Ip's master, Chan Wah-shun. Ip proceeded to train with Leung Bik,[10] until Leung's death in 1911.[11]