Dennis To Yu-Hang as Ip Man

Crystal 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

Ip Chun as Leung Bik

Sammo Hung Kam-Bo as Chan Wah-Shun

Bernice 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

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

Jun as Young Ip Man

Zhang Chi as Sui San

Zhu Xueliang as Yao Choi

Ding Xiaolong as Rogue

Yang Qingqian as Acrobatic Girl

Michelle Fang Tingting as Flirtatious Lady

Dang Shan-Peng as Japanese Killer

Gus Lim as Japanese Killer

Andy Taylor as Foreign Student

Hins Cheung King-Hin as Mr Cho

Louis Cheung as Customs Officer

Lee Lik-Chi as Translator