Hailing from a rich family, Ip Man devoted his life to practicing Wing Chun in the city of Foshan. When Gong Baosen, Chairman of the Chinese Martial Artists Union, decides to mark his retirement with a sparring match in Foshan, Ip is thrust into the limelight as Baosen's chosen opponent. Despite objections by Baosen's daughter Gong Er, Baosen goes ahead with the match and and breaks his family's unbeaten record with a rare loss. Gong Er manages to save her family honor by winning a rematch against Ip, and the two even strike up an unspoken bond in the process. However, the Sino-Japanese War breaks out, causing Ip to lose his family fortune and Baosen's disciple Ma San to turn to the Japanese for self-preservation. While Ip struggles to care for his family, Gong Er makes a major sacrifice in the name of revenge. Meanwhile, a mysterious man named The Razor attempts to leave behind his life as a spy and heads to Hong Kong...