Anthony Wong Chau-Sang as Ip Man

Anita Yuen Wing-Yee as Cheung Wing-Sing

Gillian Chung as Chan Sei-Mui

Jordan Chan Siu-Chun as Tang Sing

Eric Tsang Chi-Wai as Ng Chung

Jiang Luxia as Lee King

Timmy Hung Tin-Ming as Leung Sheung

Zhou Chuchu as Jenny

Xiong Xinxin as Local Dragon

Marvel Chow as Wang Dong

Ip Chun as Stall owner with phone

Liu Kai-Chi as Lee Yiu-wah

Cho-Lam Wong as Blind Chan

Jonathan Wong Chi-Hin as Ni Tang

Leo Au-Yeung as Fat Choi

Aki Chan as Worker

Cho Kwai Chee as Queen Mary Hospital Doctor

Kevin Cheng Ka-Wing as young Ip Man

Queenie Chu Wai-Man as So Fei

Ash Gordey as Superintendent of Police

Junlica as Worker

Lam Chi-Kit as Dentist

Yiu Kin Kong as Disciple of Pak Hok Pai

May Law Koon-Lan as Lee Yiu-wah's wife

Ken Lo Wai-Kwong as Wei Batian

Joe Luk as Luk Fu

Au Tsui Yea Maggie as Queen Mary Hospital Nurse

Mang Hoi as Chess Onlooker

Mulhall as Disciple

Donny Ng as Ng Chan

Wang Qinxi as Daughter of Lee Yiu-wah

Sebastian as Disciple

Kasey Tang as Worker

Chalie Wong as Worker

Donny Wu as Wu Zan

Jia Hui Wu as Loan-shark

Ding Xiaolong as Monkey

Liang Xinwen as Daughter of Lee Yiu-wah

Xu Huangli as Yiu-Wah's second daughter

Lu Yang-Yang as Lee Yiu-Wah's daughter

Chen Yan-Xi as Lee Yiu-Wah's son

Junjie Zhang as Disciple of Ip Man

Zhang Songwen as Yip Chun

Lv Ziying as Son of Chan Sei Mai

Fung Hak-On as Chess Onlooker