Dennis To Yu-Hang as Ip Man

Huang Yi as Cheung Wing Shing

Yuen Biao as Ng Chung So

Louis Fan Siu-Wong as Ip Tin-chi

Rose Chan Ka-Wun as Li Mei Wai

Sammo Hung Kam-Bo as Chan Wah-Shun

Ip Chun as Leung Bik

Bernice Jan Liu as Kitano Yumi

Lam Suet as Deputy Mayor Cheung Ho-Tin

Xu Jiao as Young Li Mei Wai

Heman Leung as Chairman Li Man Ho

Jun as Young Ip Man

Shen Al Jie as Young Ip Tin Chi

Sire Ma as Cheung Wing-Wah

Joseph Lee Kwok-Lun as Sheriff

Kenya Sawada as Kitano Yukio

Chen Zhihui as Ip's Father

Ding Xiaolong as Rogue

Lena Yang as Acrobatic Girl

Hins Cheung King-Hin as Mr Cho

Louis Cheung as Customs Officer

Lee Lik-Chi as Translator

Zhang Chi as Sui San

Zhu Xueliang as Yao Choi

Song Kai as