Martial arts grandmaster Ip Man, is known as the grandmaster of the Wing Chun fighting style and more popularly as Bruce Lee’s former master. Donnie Yen’s portrayal as Ip Man in Ip Man (2008), would kick start a series of movies, sequels, and spin-offs revolving around the life and times of the iconic grandmaster.
There are overall nine Ip Man movies. Director Wilson Yip and actor Donnie Yen created the Ip Man franchise which consisted of Ip Man (2008), Ip Man 2 (2010), Ip Man 3 (2015), and Ip Man 4: The Finale (2019). Director Yuen Wo Ping created a spin-off with Master Z: Ip Man Legacy (2018). Director Herman Yau created his own franchise with The Legend is Born: Ip Man (2010) and its sequel Ip Man: The Final Fight (2013). There are also two standalone films namely, The Grandmaster (2013) and Ip Man and Four Kings (2019).
Best order to watch Ip Man Movies
The Ip Man movies are not all connected chronologically except for the Wilson Yip – Donnie Yen franchise, and the Herman Yau franchise. As Master Z: Ip Man Legacy (2018) is a spin-off from Ip Man 3 (2015), that movie is best watched together with the main four. As the remaining two movies are standalone, they can be watched at any sequence. Ideally, below is the best order in which to watch the Ip Man movies:
- Ip Man – (2008)
- Ip Man 2 – (2010)
- Ip Man 3 – (2015)
- Master Z: Ip Man Legacy – (2018)
- Ip Man 4: The Finale (2019)
- The Legend is Born: Ip Man – (2010)
- Ip Man: The Final Fight – (2013)
- The Grandmaster – (2013)
- Ip Man and Four Kings – (2019)
Ip Man movies in order
1. Ip Man – (2008)
Set in the 1930’s Foshan, China, Ip Man lives a modest life living in a mansion-like home with his wife and daughter. The Second Sino-Japanese War turns Ip’s world upside down. As food becomes scarce, Ip works in a coal mining factory to support his family, where he witnesses his friend executed by the Japanese army, during a martial arts exhibit in exchange for food.
In an act of aggression, Ip challenges 10 Japanese fighters and defeats them. General Miura witnesses Ip’s feat and attempts to enlist him to train his Japanese soldiers. Ip refuses and eventually, a duel between him and Miura takes place in the town center.
Ip wins the fight, which led to him being shot in the shoulder by Sato (Miura’s second in command). The act incites the Chinese crowd who scuffles with the Japanese soldiers. Amidst the chaos, Ip escapes with his family to Hong Kong with help from a friend.
2, Ip Man 2 – (2010)
Set after the events of the first film, Ip Man’s family escapes to Hong Kong where he plans to start life anew by teaching Wing Chun. Ip gains a small group of students where he eventually meets a local martial arts master; Master Hung.
Hung informs Ip that in order to teach martial arts in Hong Kong, he must first accept challenges from the local masters and defeat them within a set time. Ip defeats the challengers and fights to a draw with Master Hung. Acknowledging his skills, Hung allowed Ip to open his own martial arts school.
Hung was involved in a boxing competition to promote Chinese martial arts. In a fight between Hung and the event’s star boxer, The Twister, Hung is beaten to death. Later in the film, Ip challenges Miller to a fight where he defeats the boxer. After the fight, Ip gives a speech to the western and Chinese audience and media, advocating for mutual respect between different races and cultures.
3. Ip Man 3 – (2015)
Set in 1959, Ip Man and his family are living in relative comfort in Hong Kong. When a local triad leader tries to acquire the land occupied by the school Ip’s son is studying in, Ip decides to guard the school. With the help of Tin-Chi (the father of a school student), they fight the triad until a troop of policemen arrives.
Ip learns that his wife (Wing-sing) has been diagnosed with cancer. Upon learning that an American boxer named Frank is the man behind the triad’s plans, Ip confronts Frank. Frank promises to leave the school alone if Ip can last in a three-minute fight against him. They fight to a draw and Frank keeps his promise.
Tin-Chi establishes his martial arts school and challenges Ip to a battle to decide who is the true Grandmaster of Wing Chun. Upon Tin-Chi’s defeat, Ip tells him the importance of spending time with family as compared to competing.
4. Master Z: Ip Man Legacy – (2018)
After being defeated by Ip Man, Tin-Chi lives a low-profile life, running a grocery store in Hong Kong. He is involved in a fight with local drug dealer Tso Sai Kit while trying to save an opium addict (Nana) and her friend Julia. Following the incident, Kit sets fire to Tin-Chi’s house. Tin-Chi then works at the Gold Bar courtesy of Julia’s brother, Fu.
Kit’s sister, Kwan, the head of the family crime syndicate wishing to transition to legal businesses, visits Tin-Chi at the Gold Bar, with the intention to compensate him for his troubles. Kit and his gang murder Nana by forcing her to overdose on heroin. Tin-Chi and Fu fight their way to the syndicate’s headquarters where they encounter Kit and Kwan. Kwan forces Kit to reveal the location of the heroin storage, where Fu then exposes the drugs to the media.
Davidson (Kit’s boss), murders Fu in an unfair fight. Tin-Chi fights and defeats Davidson where he regains his confidence in using Wing Chun for good.
5. Ip Man 4: The Finale – (2019)
In 1964, upon discovering he has throat cancer, Ip Man travels to San Francisco in search of academic opportunities. There, his student Bruce Lee had opened a Wing-Chun school, which enraged Grandmaster Wan, the president of the Chinese Consolidated Benevolent Association.
Meanwhile, a US Marine and student of Lee’s tries to convince Barton Geddes, an Army Sergeant, to incorporate Chinese martial arts into their hand-to-hand combat training. Geddes sends the Marines’ Karate instructor, Colin Frater to challenge the association’s grandmasters where he defeats most of them until Ip beats him up badly. Upon seeing Frater at the hospital, Geddes orders for Wan’s arrest and fights Wan at the Marine camp.
After learning of Wan’s defeat at the hands of Geddes, Ip defeats Geddes in a long and savage fight. Ip decides to return to Hong Kong. He instructs his son to film him as he demonstrates Wing Chun in the wooden dummy. Ip dies of cancer at the age of 79 in 1972.
6. The Legend is Born: Ip Man – (2010)
Set in 1905, a young Ip Man, along with his adopted brother Ip Tin-Chi, learns Wing Chun from Master Shun’s academy. There they meet Mei-wai and the three of them are involved in a love triangle. After the death of Master Shun, Ip’s senior Ng Chung-sok teaches in his stead. Ip eventually leaves Foshan to study in Hong Kong. Over the course of his time in Hong Kong, Ip meets a Master Bik, who teaches him a varied and improved style of Wing Chun.
Upon Ip’s return to Foshan after five years and reunites with his peers. Tin-Chi, who is actually a Japanese undercover agent, murders Mei-wai’s godfather. Upon learning that Chung-sok has learned his secret, Tin-Chi and the Japanese attempt to assassinate Chung-sok.
Ip arrives in the knick of time to save Chung-sok and subsequently defeats the Japanese and Tin-Chi. Tin-Chi performs seppuku and Ip discovers that the Japanese have been smuggling Japanese children into China, possibly as potential undercover agents.
7. Ip Man: The Final Fight – (2013)
In 1949, Ip Man, who has been suffering from chronic gastric pain, travels to Hong Kong where he teaches Wing Chun and gained a number of new students. Ip Man struggles against the vicissitudes of life, as well as his wife’s death in Hong Kong.
While teaching Wing Chun, he copes with his gastric pain and develops a relationship with the local singer, Jenny. When his student gets in trouble with the mob boss, namely Local Dragon, Ip shows up to defeat Long Dragon and turns him over to the police.
At the end of the movie, Ip is seen practicing Wing Chun on a wooden dummy while his son, Ip Chun records it on a camera. The film also shows viewers the actual footage of the real-life Ip Man doing the same thing.
8. The Grandmaster – (2013)
Ip’s peaceful existence is threatened by the arrival of Gong Yutian, a grandmaster from Northern China, who announces that he has retired and appointed Ma San as his heir in the North. Ip, representing the Southern masters, challenges Gong Yutian and wins the fight. Gong Er (Gong Yutian’s daughter) challenges Ip in an effort to regain her family’s honor. She wins the fight and they part on friendly terms.
Ma San betrays and kills Gong Yutian on a political agenda. Gong Er eventually defeats Ma San in vengeance for her father’s death. In 1952, Ip and Gong Er meet for the last time, where she confesses that she has harbored romantic feelings for him since their first fight. Ip learns that she died in 1953 due to her long-term injury from the fight with Ma San. Ip’s Wing Chun school becomes successful and a young Bruce Lee enrolls to learn under him.
9. Ip Man and Four Kings – (2019)
Set in the 1950s, Ip Man sets up a Wing Chun martial arts school in Hong Kong. In the meantime, Master Fang, a local martial arts grandmaster, had been investigating the disappearance of his sister. Upon discovering Zheng’s slavery den, Master Fang is killed.
Zheng frames Ip for the murder of Master Fang. Ip is imprisoned by the police but subsequently, a mysterious person helps him escape from his prison cell. The mysterious person turns out to be an escort for Zheng’s business associate who frequents Zheng’s business proceedings.
In an effort to prove his innocence and to stop Zheng’s triad, Ip has to take down the heads of the prostitution, alcohol, gambling, and catering syndicates (also known as the Four Heavenly Kings). After defeating them, Ip heads to Zheng’s hideout where he defeats him and his guards.