While enrolled at St. Stephen's, a classmate, hearing of Yip's training in kung fu, dared him to challenge an old kung fu practitioner living on a boat anchored in Hong Kong Bay. Yip accepted the dare and duly sought out and challenged the old man. The old man accepted his challenge and, despite Yip's growing reputation as an unmatched fighter, beat him handily. Only after his defeat did Yip discover that the old man was actually master Leung Bik, a direct descendant of the original wing chun lineage reaching back to Wing Chun herself. After the melee, Leung took Yip as his only student in the art and advanced his wing chun even further, both expanding his theoretical grounding in the art and his refining his technique. (Another version of Yip Man's biography omits the story of the challenge while still confirming that Yip met Leung in Hong Kong and became his student. Yet a third version suggests that Leung himself contrived to meet Yip and invite him to train.)

Grandmaster Yip Man returned to Fashan at age 24 and found a position as the Captain of the Local Police Patrols of Namhoi. Yip Man worked as a law enforcement officer for several years teaching Wing Chun in his spare time, but always, in accordance with Wing Chun tradition, restricting his lessons to a just a few carefully selected students. Yip Man's first private student was a silk merchant named Chow Ching Chung, who hired Yip on the basis of his martial arts reputation.

Yip Man continued teaching in this manner until China succumbed to the communist revolution in 1949. Yip Man felt forcedto flee mainland China and return to British-occupied Hong Kong.

Reaching Hong Kong alone and destitute, facing certain poverty, Yip Man quickly fell back on his martial arts expertise to earn a living. He decided to break with the Wing Chun tradition of limiting instruction to a select few and opened a public Wing Chun school in the union hall building for restaurant workers. Yip Man opening the school on his own, relying soley on his own ideas and resources to get underway. Yip Manencounters an old friend, Chung Choui, who is teaching martial arts at two locations and invites Yip Man to take over the instruction at one of them so that he could support himself. It was Leung Shan who taught kung fu at a school "on the premises of the Restaurant Worker's Union in Hong Kong." There Leung provided Yip Man with a small apartment and saw to his personal needs. Yip Man would often watch the classes Leung hosted every night after the restaurant closed. Yip Man made a habit of poking light-hearted fun at Leung and the White Eyebrow kung fu taught as he watched. After taking this ribbing for some time without reaction, Leung finally became fed up and challenged Yip so as to teach him a lesson. Though Leung was younger and larger than his opponent, he was no match for the Wing Chun Yip Man had spent a liftime perfecting and "was easily defeated." Upon besting him in combat, Yip revealed himself to be a Wing Chun grandmster and took Leung as his first Hong Kong student.

When Yip arrived in Hong Kong he met up with "his good friend Hui Yee, the Chairman of the Restaurant Union," who knew of Yip Man's martial arts background and subsequently invited him to teach martials arts for the Union. Yip Man accepts the invitation and conducts wing chun classes "on the roof of the apartment where the Restaurant Union was." However Yip Man established his teaching practice in Hong Kong, he managed to create with it the seeds of a martial arts revolution that, through the efforts of some of those he taught, would take root in countries spanning the world. Though Yip Man himself never taught outside the Chinese sphere of influence, his disciples carried his wing chun around the globe. Among those who helped spread wing chun, Sifu William Cheung, a student Yip Man taught in his home for a number of years, went on to found the World Wing Chun Kung Fu Association and demonstrate wing chun in the United States and Australia.

Students, took Wing Chun to the United States. Victor Kan Wah Chit, who studied under Yip Man in the 1950s, began teaching Wing Chun in London, England, in 1975. And Leung Ting, whom Yip Man accepted as a private student in the the late 1960s, went on to form the International Wing Tsun Martial-Art Association, an organization which has become, according to material in the Wing Chun Archives, the largest Chinese martial arts organization in existence today, boasting members from nearly fifty countries the world over.

It was Yip Man's personal misfortune that drove him to teach Wing Chun publicly. Had he been able to retain his family fortune, "as a man of property, he probably would have remained a leisurely patriarch practicing wing chun in Fatshan in southern China." Yip Man's loss has become the martial arts community's gain, his misfortune compelling him to preserve and propagate a centuries-old fighting system that without him might well have passed into oblivion unheralded and uncelebrated.

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