Chen Zhihui as Master Liu
2008 – Age: 37 | 2022 – Age: 51
Chen Zhihui as Master Liu, a martial arts master of Foshan who turns to prizefighting when the Japanese invade to support himself. Sato kills him when he tries to claim a reward despite forfeiting a match.
Calvin Cheng as Chow Kong-Yiu
2008 – Age: 18 | 2022 – Age: 32
Calvin Cheng as Chow Kong-yiu, the son of the cotton mill owner, who is interested in learning kung fu from Ip Man.
Wong You-Nam as Yuan
2008 – Age: 24 | 2022 – Age: 38
Wong You-nam as Yuan, the second son of a restaurant owner in Foshan who causes a lot of trouble and often fights with his brother.
Xing Yu as Lin
2008 – Age: 29 | 2022 – Age: 43
Xing Yu as Lin, the first son of a restaurant owner in Foshan, a gifted martial artist and Ip Man’s closest friend.
Simon Yam as Chow Ching-Chuen
2008 – Age: 53 | 2022 – Age: 67
Simon Yam as Chow Ching-chuen, a businessman and Ip Man’s acquaintance who borrows money from him to set up a cotton mill.
Fan Siu-Wong as Jin Shanzhao
2008 – Age: 34 | 2022 – Age: 48
Fan Siu-wong as Jin Shanzhao, an aggressive northern martial artist who comes to Foshan to challenge other masters, hoping to set up a school and climb out of poverty. When the Japanese invade, he forms a gang of bandits and is eventually chased out of Foshan by Ip Man.
Gordon Lam as Li Chiu
2008 – Age: 38 | 2022 – Age: 54
Gordon Lam as Li Chiu, a police officer and Ip Man’s acquaintance. He becomes a translator for the Japanese officers when they occupy Foshan despite being labeled a traitor by his neighbors.
Tenma as Shibuya as Colonel Sato
2008 – Age: 39 | 2022 – Age: 53
Tenma Shibuya as Colonel Sato, a Japanese colonel and Miura’s second in-command. Unlike Miura, he is sadistic and cruel.
Hiroyuki Ikeuchi as General Miura
2008 – Age: 31 | 2022 – Age: 45
Hiroyuki Ikeuchi as General Miura a Japanese general and Karate expert, who is eager to assert the dominance of his native traditions over those of the Chinese.
Lynn Hung as Cheung Win-Sing
2008 – Age: 27 | 2022 – Age: 41
Lynn Hung as Cheung Wing-sing, Ip Man’s wife.
Donnie Yen as Ip Man
2008 – Age: 44 | 2022 – Age: 58
Donnie Yen as Ip Man, the son of a wealthy family and Foshan’s only practitioner of the martial art form known as Wing Chun.
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