In 1959, Ip Man is settling into his low-profile life in Hong Kong. The film begins with Ip Man practicing his wooden dummy techniques and a butterfly flew and sat atop the wooden dummy. This will later be revealed to contain the entire plot of the movie about his wife's passing.
The opening subtitles expressed that his elder son, Ip Chun has returned to Foshan to study, leaving him with his younger son Ip Ching and his wife Wing-sing.
A young Bruce Lee visits Ip and asks to become one of his students. After demonstrating his speed to Ip, Ip neither accepts nor rejects him and tells him to "come back later". Ip Ching is seen fighting with another boy, Cheung Fung at school, with both boys ending up with minor injuries. Wing-sing along with Ip is asked by Miss Wong, the boys' class teacher, to go to the school. As an apology, the Ips invite Cheung Fung to their home for dinner. At Ip's house, Cheung Fung displays rudimentary yet impressive Wing Chun skills. When Ip asks the boy who his mentor is, he says that it is his father, Cheung Tin-chi. Cheung shows up to pick up his son shortly after.
Cheung is seen participating in black market boxing matches and having a streak of victories. The organiser, Ma King-sang, a local triad leader, also works for Frank, an American property developer. Frank orders Ma to acquire a piece of land occupied by the school where Ip Ching and Cheung Fung study. Ma assures that it will be done within two weeks. Meanwhile, Frank is impressed by Cheung's Wing Chun skills.
The next day, when Ip is going to pick up his son from school, he witnesses Ma and his men coercing and beating the headmaster who refuses to sell them the school. Ip interferes and beat Ma to a pulp, but is forced to let Ma go as Ma's men are holding Miss Wong at knifepoint. Ip seeks help from Fatso, a close friend of his and a local police detective. Fatso agrees to help but claims a shortage of manpower. Ip agrees to guard the school alongside his students.
That night, Ip and his students watch the school compound. Lik, Ip's oldest student develops a crush on Miss Wong, but the latter promptly rejects his advances. Immediately after that, Ma's men invade the compound. Although Ip and his students are able to fight them, they are still outnumbered as the gang manages to kidnap the headmaster and set fire to a few classrooms. Cheung who happens to pass by helps fight off the invaders and also rescue the headmaster. Cheung's skills impress Ip.
Tin, a local martial arts master and Ma's former mentor, is enraged by Ma's unscrupulous acts and accompanied by Ip, confronts Ma at the shipyard and slaps him in front of his men. Ip stops Ma from stabbing Tin. Fatso arrives and keeps the situation at bay.
The humiliated Ma offers Cheung a job: to get revenge against Tin on his behalf. Desperate for money to open his own martial arts school, Cheung accepts the offer. Meanwhile, Wing-sing is diagnosed with cancer.
Cheung fights Tin in his umbrella shop, who fails to defend himself against his assailant's swift blows and ends up in the hospital with a broken arm. Ip receives a call from the hospital and visits Tin. Upon knowing that Tin did not call him, Ip realises that it was a set-up by Ma to lure him away from the school so that his gang can kidnap some of the students including Ip Ching and Cheung Fung. Ip arrives at Ma's shipyard surrounded by Ma's men. Ma, who is holding Ip Ching at knifepoint, threatens to sell the kids off to slavery if the headmaster still refuses to surrender the school. Upon knowing that his son was also kidnapped, Cheung arrives at the scene and fights alongside Ip. Ip and Cheung are able to hold their own until a troop of policemen led by Fatso comes to arrest the gang, while Ma flees but is later fired by Frank. Frank sends a proficient Thai boxer after Ip instead.
Returning home, Ip is told by Wing-sing about her condition and that she can only live for six more months. While taking Wing-sing to the clinic, Ip is attacked by the Thai boxer. Ip defeats the boxer after a few moves. Fatso later tells Ip about Frank who wants to eliminate Ip at all costs for obstructing his plans. Ip decides to confront Frank in his office. Frank challenges Ip to a three-minute fight—if Ip can withstand his fists for three minutes, he would leave the school, Ip and his family alone; Ip accepts the challenge. From the outset, Ip is seemingly overwhelmed by the sheer muscle and force of Frank who dominates the fight thoroughly. Realising he is no match for Frank in terms of hand speed and power, Ip attacks Frank's footwork instead and is able to launch a few punches on him. Just as both are about to launch a decisive blow on each other, three minutes had passed. Ip leaves the office and Frank keeps his promise, seemingly impressed.
Cheung opens his martial arts school and claims that his Wing Chun is genuine while Ip's isn't. Cheung proceeds to defeat a number of martial arts masters and becomes famous on the news. Finally, he challenged Ip to a battle that shall decide who will be the Grandmaster of Wing Chun. Meanwhile, Ip spends more time with his dying wife. On the day of the match, Ip chooses not to attend, but instead goes out dancing with Wing-sing (after having been taught a few moves by Lee, whom Ip finally accepts as disciple). Some of those who attend the match are made impatient as Cheung waits for his opponent. Ultimately, Cheung is declared the winner owing to Ip's failure to attend. Wing-sing, despite being happy about Ip's decision to accompany her, makes an appointment with Cheung for another match on Ip's behalf; she knew that Ip would have attended if not for her condition.
Wing-sing accompanies Ip to the fight. They first fight with poles which Ip and Cheung fought to a standstill. They then fight with knives with Ip seeming to win narrowly. When Cheung lost his knives, Ip throws his away and then proceeds to fight without weapons. They both seem evenly matched, with both delivering blows to each other. However, Cheung successfully lands a blow to Ip's right eye, temporarily blinding him. Cheung's victory seemed certain, but Ip evades Cheung's following hits with his hearing and counters Cheung with a one-inch punch, despite not being able to see. Defeated, Cheung relinquishes his title as the Grandmaster of Wing Chun. Ip remarks that "what's most important are the ones closest to us", and leaves.
The ending of the film reveals that Wing-sing had passed away in 1960, and Ip made Wing Chun well known internationally.[6]
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