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Ip was a member of the Kuomintang, and according to rumors, he joined the Central Bureau of Investigation and Statistics in its academy in Guizhou in 1938, after which he would have returned to Foshan as an undercover intelligence officer. He married Cheung Wing-sing and they had several children: sons Ip Chun and Ip Ching and daughters Ip Nga-sum ( 葉雅心) and Ip Nga-wun ( 葉雅媛). He taught Wing Chun to several of his subordinates, friends and relatives, but did not officially run a martial arts school. Ip returned to Foshan in 1916 when he was 24 and became a police officer there for the Nationalist government. Ip proceeded to train with Leung Bik, until Leung's death in 1911. 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.
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A week later, Lai told him that the man he had fought was asking after him. Discouraged by his defeat, Ip left without a word and afterward was so depressed that he did not dare mention that he knew Kung Fu. Incredulous at the speed with which he had been countered, Ip requested a second duel and was beaten again, just as soundly. The man was Leung Bik and he easily overwhelmed Ip Man. He went to Lai's house on a Sunday afternoon and, after exchanging brief pleasantries, challenged the man to a duel. At the time, Ip was undefeated so he eagerly accepted the challenge. 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. Stephen's College, a secondary school for wealthy families and foreigners living in Hong Kong. Īt the age of 16, with help from his relative Leung Fut-ting, Ip moved to Hong Kong and there he attended school at St. Ip learned most of his skills and techniques from Chan's second most senior student, Ng Chung-sok ( 吳仲素). 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. Chan was 57 at the time, and Ip became Chan's 16th and last student. Ip started learning Wing Chun from Chan Wah-shun when he was 9 or 13. 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). 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.