Production notes

Ip Man 2 is the second feature film overall to be based on the life of Ip Man, following the previous film Ip Man. The sequel is the fifth film collaboration between director Wilson Yip and actor Donnie Yen. Ip Man 2 was produced by Raymond Wong and distributed by his company Mandarin Films upon its theatrical release in Hong Kong. It was the last film Wong produced under his Mandarin Films production banner. Wong's son, Edmond Wong, returned to write the screenplay. Along with appearing in a supporting role, Sammo Hung reprised his role as the film's martial arts choreographer. Kenji Kawai reprised his role as the film's music composer.

Prior to Ip Man's theatrical release in December 2008, producer Raymond Wong announced plans to develop a sequel to the film. The sequel was intended to focus on the relationship between Ip Man and his most famed disciple Bruce Lee. In March 2009, Wong announced that the Lee character might not appear in the sequel, as producers had not fully finalized negotiations with Lee's descendants on the film rights. In July 2009, it was announced that Ip Man 2 would focus on a young Bruce Lee, prior to Lee becoming Ip Man's most famed disciple. The sequel continues Ip Man's story, focusing on his move to Hong Kong as he attempts to propagate Wing Chun in the region.

Several cast members from Ip Man reprise their respective roles in the sequel. Donnie Yen reprises his role as Ip; Lynn Hung reprises her role as Cheung Wing-sing, Ip's wife, who is now pregnant with their second child. To prepare for her role in the film, Hung asked producers for a 10-pound prosthetic belly to portray the feeling of being pregnant. Hung stated that the difficulty of her role lay in playing someone who goes from "a naive and simple-minded young woman to a strong, understanding and supportive adult." Fan Siu-Wong reprises his role as Jin Shanzhao, Ip's aggressive rival in the first film. In the sequel, Jin attempts to retire from the martial arts world by becoming an ordinary citizen; he later befriends Ip. In a cameo appearance, Simon Yam reprises his role as Ip's friend Chow Ching-chuen, who is now a mentally disabled beggar. Li Chak reprises his role as Ip Chun, Ip and Wing-sing's son. Sammo Hung was announced as part of the cast in April 2009. Apart from serving as the film's martial arts choreographer, Hung appears as Hung Chun-nam, a master of the southern Chinese martial art of Hung Ga. In August 2009, it was announced that Huang Xiaoming would be playing Wong Leung, a supporting character based on Wong Shun Leung, one of Ip Man's disciples and the person responsible for mentoring Bruce Lee. Former child star Ashton Chen was also announced to be playing a disciple. Veteran actor Kent Cheng also has a supporting role in the film. To Yu-hang, who had a supporting role in the first film, appears in the sequel as a different character named Cheng Wai-kei. Cheng is a gang leader practicing Hung Ga, who decides to exact revenge on Wong after Wong defeats Cheng in a fight. Wilson Yip commented on the casting of the veteran actors as being "a form of tribute to old school kungfu movies." Yen and Yip reportedly conducted a worldwide casting call for a suitable candidate to play Lee, who is Ip Man's most celebrated disciple. The film briefly portrays Lee at the age of 10. Yip and Yen debated over whether to look for an actor with a solid martial arts foundation or looks. Among the 1300 Mainland Chinese candidates auditioning for the role, Yip narrowed the casting call to two possible candidates: 10-year-old Jiang Dai Yan from Henan and 12-year-old Pan Run Kang from Heilongjiang. On 10 August 2009, it was announced that Jiang Dai Yan would be playing the role of a 10-year-old Bruce Lee. While the Bruce Lee character makes a brief appearance in the film, director Wilson Yip has expressed interest in making a third film that will focus on the relationship between Ip and Lee. Yen, however, has stated his lack of interest in making a third film, feeling that Ip Man 2 will "become a classic." In November 2008, Yip revealed that there would be another actor appearing in the film, a martial artist who has been a fan of Donnie Yen. Yip commented, "I can only say that he fights even more vehemently than Sammo Hung." However, in February 2010, it was revealed that British actor and stunt performer Darren Shahlavi would have a supporting role as a boxing opponent fighting against Ip Man. Yip later stated that Shahlavi's character "has his own drama. He is also a personage, not just some random foreign guy that appears from nowhere for the sake of getting beaten up, like you see in other films." Other cast members include Ngo Ka-nin and Kelvin Cheng.

The filmmakers stated that while Ip Man was about survival, Ip Man 2 is about living. The sequel is set in Hong Kong in 1949, when the city was under British colonial rule. Screenwriter Edmond Wong stated that the film also explorers "how Hong Kong people were treated under British colonial rule, and Western attitudes concerning Chinese kung fu". Wilson Yip stated that Ip Man 2 is a much better film than its predecessor in terms of characterization and storyline. The film focuses on disputes between the disciples of Hung Ga and Wing Chun martial arts, as well as the conflict and rivalry of the two practitioners. Wing Chun, as taught by Ip Man, is being viewed as a martial art meant only for girls; Hung Ga, as taught by Hung Chun-nam, is being seen as a macho form of boxing. Of the two characters, Yip commented, "Sammo Hung's character is not exactly villainous, but he's very overbearing, just like his torrential Hung Ga. In contrast, Ip Man is very unassuming, much like his fist." Yip also stated that the film has some moments of "family drama", such as the ongoing conflict between Ip and his wife Wing-Sing.

Prior to filming, a production ceremony for Ip Man 2 was held in Foshan, receiving plenty of media coverage. Principal photography began on 11 August 2009; filming took place in a sound stage at Songjiang Studios in Shanghai. On 28 October 2009, reporters were invited to the set to view the anticipated duel between Donnie Yen and Sammo Hung as it was being filmed. Filming ended on 8 November 2009.

The film's martial arts sequences were choreographed by Sammo Hung, who also worked on the choreography for the first film. Prior to principal photography, Hung had undergone a major cardiac surgery. When he returned to the set, his dramatic scenes in the film were filmed first, with his fight sequences being filmed last. Hung performed his own stunts in the film, which led to him receiving several injuries during filming. While filming a scene, Hung was struck in the face by co-star Darren Shahlavi. He insisted on completing the shoot before going to the hospital. Not wanting his injuries to hinder the production progress, Hung spent five hours trying to complete the scene before going to the hospital for four stitches. After the completion of filming, Hung expressed that he was dissatisfied with the fight sequences involving his character, presumably due to his heart condition. He also stated that he plans to challenge Yen in a future film: "Although I'm the martial arts choreographer, our moves were all rather regulated, being confined by the script. So, I made a pact with Donnie Yen to have a rematch next year if the opportunity arises." Huang Xiaoming prepared for his role by learning Wing Chun martial arts. He turned his hotel room into a gym, practicing with weights and a wooden dummy. Huang received multiple bruises on his arms, due to his frequent practices on the dummy. Huang would also spend time practicing with the film's stunt team, under Jun Gao. Wilson Yip praised his performance in the film, stating that Huang "may not be a martial artist, but he specially ordered a wooden dummy, and trained daily at home. In the end, he is doing the action scenes better than Hiroyuki Ikeuchi in the first film."

The Chinese title of the film (traditional Chinese: 葉問2:宗師傳奇; simplified Chinese: 叶问2:宗师传奇) literally means Ip Man 2: Legend of a Grandmaster. The title is a play on the first film's working title which was Grandmaster Ip Man, a title that was changed when Wong Kar-wai clashed with producers while trying to make his own Ip Man biopic. Wilson Yip explained that the title of the film was coincidental rather than intentional: "The sequel is about Ip Man being elevated from a master, a hero to a grandmaster, so we have 'grandmaster' in the title." Wong Kar-wai's film, titled The Grandmaster, was released in January 2013.