[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).

[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.

[3] He taught Wing Chun to several of his subordinates, friends, and relatives, but did not officially run a martial arts school.

Noted students of this time were Lok Yiu, Chow Kwong-yue (周光裕), Kwok Fu (郭富), Lun Kah (倫佳), Chan Chi-sun (陳志新), and Lui Ying (呂應 ).

Chow Kwong-yue was regarded as most talented of Ip's Foshan students, but he devoted himself to trade and abandoned the martial arts.

Kwok Fu and Lun Kah began teaching and spreading the art of Wing Chun in the Foshan and Guangdong region.

[12][additional citation(s) needed] During the second Sino-Japanese war, Ip Man sided with Kuomintang during the conflict.

It is rumoured that he had 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.

Ip's only prior experience was as a policeman in Foshan, but he was either unable or refused to join the Hong Kong Police Force.

[18][19] Ip began teaching Wing Chun in the early 1950s, to escape poverty and to allegedly feed his opium addiction.

[19][20][21][22] His earliest students consisted mainly of "poor and uneducated" members of the Restaurant Workers' Association[16] and "restless and angry young men", who were attracted to Ip Man's charismatic personality and the prospect of getting tougher in order to survive the dangerous environment of 1950s Hong Kong.

He moved his school twice, first, to Castle Peak Road in Sham Shui Po, and then to Lee Tat Street (利達街) in Yau Ma Tei by where only a few of his former students follow and continue to train under.

[28][29][30] The main purpose of the Ving Tsun Athletic Association was to help Ip tackle his financial difficulties in Hong Kong,[31] which was due to his regular use of opium.

Ip died on 2 December 1972, in his unit at 149 Tung Choi Street in Hong Kong,[1] from laryngeal cancer, only seven months before the death of Bruce Lee, his most famous student.

Ip's notable students include Chu Shong-tin, Lok Yiu, Wong Shun-leung, Bruce Lee, Moy Yat, Ho Kam Ming, Victor Kan, Lo Man-kam, William Cheung, and Leung Ting.

Ip Man, a Hong Kong film starring Donnie Yen as the martial artist, was released in 2008.

Herman Yau directed the film and it starred Dennis To as Ip Man and Seventeen band's Wen Junhui as his younger counterpart.

The film focuses more on the end of an era in Chinese martial arts history as the Second Sino-Japanese War broke out.

It was directed by Fan Xiaotian and starred Kevin Cheng as the eponymous character and Zhou Jianan as the younger counterpart.

[41] In the 2018 action-comedy film Kung Fu League, Dennis To returned in the role of Ip Man, with three other martial artists, Wong Fei-hung, Huo Yuanjia, and Chen Zhen, whisked through time to teach martial arts to a modern-day comic book artist caught in a love triangle.