The first Ip Man movie started off with a bang by showcasing Ip Man’s incredible Wing Chun fighting prowess against Master Liu, of the Liu Fist Sect. The mutual admiration, kindness, and friendliness between the two fighters is apparent from the very first moment.
When Master Liu asks for a private match against Ip Man, the two battle it out, with the latter exercising extreme restraint so as not to harm Master Liu. Though he easily overpowers his opponent, Ip Man displays humility by thanking Liu for “allowing him to win.”
Ip Man Vs. Jin – Ip Man (2008)
When a cocky band of Kung Fu fighters led by the arrogant Jin shows up in Fo Shan to battle the martial arts masters and establish their dominance, there’s only one guy left standing in their way – Ip Man.
When Jin challenges Ip Man to a fight, it’s an adrenaline-pumping display of fighting prowess between two seasoned experts. Ip Man gains the upper hand and humbles Jin, setting the stage for two future encounters that would give him a change of heart… and attitude!
Ip Man Vs. Ten Men – Ip Man (2008)
After Japan’s occupation of Fo Shan, the city goes to hell, leaving many Chinese with barely enough food to survive. The ruthless General Miura sets up an underground martial arts fight pit where he allows Chinese fighters to compete for bags of rice.
When Ip Man learns that both his friends Lin and Master Liu have been killed by Miura and his second-in-command, he demands to fight ten men as a means of showing Miura his power. The theme of Ip Man fighting ten men would later be revisited in Ip Man 3.
Ip Man Vs General Miura – Ip Man (2008)
When Ip doesn’t return to the arena, Miura sends Satō and two soldiers to hunt him down. After defeating them at the apartment, Ip and his family run away and hide at Lee’s house. The Japanese learn about the cotton factory and take the workers hostage. Despite Lee’s warnings, Yip surrenders to the Japanese while arranging for his wife and son to be sent to Hong Kong for protection. Miura asks Ip to train Japanese soldiers in Chinese martial arts, but Ip refuses and challenges Miura to a duel. Though Satō insists on Ip’s execution, Miura accepts the challenge to uphold his honor and crush the Chinese spirit; Satō threatens Ip with death if he doesn’t let the general win.
In front of the people of Foshan, Yip defeats Miura after a long and hard battle.
Upon arriving in Hong Kong, Ip Man and his wife and child are left poor and struggling. When Ip Man tries to open a Wing Chun school, he faces several setbacks, not the least of which is the pecking order of the martial arts schools in Hong Kong.
In order to be allowed to teach Wing Chun, Ip Man is tasked to prove his worthiness. He does so by battling several Kung Fu masters on top of an unbalanced desk, holding his own until the incense burns out, which ultimately gains him their respect.
Hung Chun-nam Vs. The Twister – Ip Man 2 (2010)
Kung Fu master Hung Chun-nam shares a combative relationship with Ip Man, a man he desperately wants to respect, were it not for the corrupting elements within his circle. When the British interference in the martial arts community becomes too insulting to bear, Hung challenges their greatest fighter to a duel, to protect the honor of Chinese martial arts.
That fighter is Taylor “The Twister” Miller, an arrogant and aggressive English boxing champion who beats Hung so badly that he succumbs both to his injuries, and his chronic asthma. His death is the catalyst for Ip Man to step in and avenge the death of his respected rival.
Ip Man Vs. The Twister – Ip Man 2 (2010)
Ip Man decides to jump into the ring to carry on Hung Chun-nam’s desire to protect the honor of Chinese martial arts from the arrogance of the British. To do so, he’ll have to defeat the man responsible for Hung’s death – The Twister.
The fight is an amazing display of the technical differences between Wing Chun Kung Fu and heavyweight boxing, with Ip Man adapting to several unfair rules put upon him by the judges, yet still emerging victorious. It’s also a very important fight, as boxers are considered by Wing Chun practitioners to be especially difficult opponents. This is due to the fact that boxers constantly protect their center-line (nose, windpipe, chest) – the primary target of most Wing Chun strikes.
Ip Man Vs. The Thai Kickboxer – Ip Man 3 (2015)
Ip Man 3 focused more on drama than action, but that doesn’t mean the series lost its edge. This was apparent in one of the best fight scenes of the film where Ip Man faces a Thai kickboxer who attacks him in an elevator, alongside his sick wife.
The fight soon spills out into the lobby where Ip Man channels all of his Wing Chun training (including basic rudiments such as rooting), to stay balanced, even on a staircase. He eventually overwhelms and beats his attacker senseless, but allows him to leave after.
Ip Man Vs. Zhang Jin – Ip Man 3 (2015)
The battle for supremacy in arrives in the final act of the third film when Ip Man is convinced by his dying wife to face his rival Zhang Jin for the title of Wing Chun Grandmaster. With the realization of his wife’s impending doom close at hand, Ip Man finds the courage to face Zhang in a battle for the top spot.
The fight is unique to the series, as it showcases the rarely-seen use of Wing Chun weapons combat, which is considered instrumental in mastering the art form. It also showcases two styles of Wing Chun – the traditional mainland style, and the one modified by Ip Man. Future practitioners would blend mainland elements into Ip Man’s style to correct certain vulnerabilities in the latter.
Po tells Ip about Frank, who wants to eliminate Ip at any cost for interfering with his plans. Ip confronts Frank in his office, where Frank promises to leave the school alone if Ip can last the full three minutes of the fight. Initially overwhelmed by Frank’s muscle and sheer strength, Yip turned the tide by attacking Frank’s lower half. They fight to a draw after three minutes; seemingly impressed, Frank keeps his promise.
Frater Vs. The Grandmasters – Ip Man 4 / 2019
Ip Man 4 took the series from Hong Kong to San Francisco where race relations became a key thematic element. A particularly noteworthy battle involves U.S. Marine Corps Karate master Frater doing battle with the Grandmasters to convince his superiors to abandon blending Chinese martial arts into their combat training.
Frater defeats several of the Grandmasters in a prolonged battle before Ip Man steps in to put an end to it. Utilizing the strength of his Wing Chun, Ip Man capitalizes on the vulnerabilities of Karate long enough to show everyone the superiority of his technique.
Ip Man Vs. Sergeant Geddes – Ip Man 4 / 2019
Scott Adkins gets a starring role in the fourth film, and he plays it up to his usual excellence as the main foe for Ip Man to battle. At first, Ip Man is overpowered by Geddes’ brutal attacks, a defeat exacerbated by the news that he has cancer.
Battling through his emotions, Ip Man summons all of his Wing Chun skills (including the devastating Chain Punch) before putting Geddes down for the count with a strike to the throat. It’s a fitting end to an amazing film series, a talented group of martial arts actors, and the lineage of a man who will stand the test of time as a true Grandmaster.