[[folder: Introduced in ''Ip Man 1'']]
!!Ip Man (Master Ip)
The titular character. Ip is a Wing Chun master whose house was seized by the Japanese. Played by DonnieYen.
* {{Badass}}
** BadassLongRobe
* BerserkButton: Will NOT stand down when defending the Honor of Chinese Warrior Culture. He also doesn't take kindly to those who threaten his family.
* BewareTheNiceOnes
* CharacterTitle
* DotingParent: Becoming poor made him closer to his family, and comes to realizes how much he loves them over Martial Arts. He even asks Master Hung in the second film "Which is more important; our battle, or having dinner with your wife and children?"
* TheFettered
* HappilyMarried
* TheHero
* HistoricalDomainCharacter: Of Yip Man, BruceLee's master.
* HonorBeforeReason
* ImprovisedWeapon: A master of this. First he uses a duster and later he uses a stick. Both against Jin.
* TheHeart: Is willing to help anyone in need in spite of his own poverty.
* MartialPacifist
* TheMcCoy
* MiseryBuildsCharacter: And makes you a more loving father.
* MrFanservice
* NiceGuy
* OneManArmy: He can literally defeat dozens of martial artists single-handedly.
* ParentalNeglect: He seems to be this at first regarding his son. To the point that his wife called him out on it.
* ProudWarriorRaceGuy: Dosen't stop him from being a gentleman and a total sweetheart, though.
* RapidFireFisticuffs: His rolling punches pack a serious wallop.
* RealMenWearPink: Granted he is garbed in black 99% of the duration of both films and never literally wears pink, but it's mentioned a few times that Wing Chun was invented by a woman. The name itself means something like "eternal springtime" or "spring chant" depending on who you ask.
* RichesToRags: He started out a rich man, then was forced to live in abject poverty when the Japanese occupied Fo-Shan.
* ShowyInvincibleHero: While he always [[CurbStompBattle curb-stomps]] his opponents, at least in the first film, he did it with such a style.
* SimpleYetAwesome: The fundaments of Wing Chun Kung Fu.
* SmokingIsCool: When he is at ease.
* TheStoic
** NotSoStoic: He was often calm and collected but he finally loses it when he saw [[spoiler: Liu being shot trying to pick up a bag of rice he won.]]
* TranquilFury
* WarriorPoet
* WarriorTherapist

!!Cheung Wing-sing
Ip Man's wife, played by Lynn Hung. She disapproves of her husband always fighting and wants him to spend more time with his family. She has two sons: Ip Chun, played by Li Chak, and Ip Ching, born at the end of the second film.
* HappilyMarried
* [[spoiler: IncurableCoughOfDeath: She starts getting abdominal pains in the third film and was eventually diagnosed as having cancer. She died after the events of the film from it.]]
* YamatoNadeshiko

!!Master Liu
A martial artist teacher who had a friendly fight with Ip. Played by Chen Zhihui.
* OvershadowedByAwesome
* ProudWarriorRaceGuy
* TheWorfEffect: He was easily defeated in his first two fights on screen. By the time he actually defeated someone, it was too little too late.

!!"Crazy/Zealot" Lin
Ip's friend who runs a teashop. Played by Xing Yu.
* HotBlooded: Deconstructed; his passionate hate against the Japanese ended up getting him [[spoiler: killed by Miura (who didn't want to kill him in the first place).]]
* TooDumbToLive: Despite the fact that he was severely injured against Miura, he continued to go on against him and ended up beaten to death.

!!Sha Dan Yuan
Lin's brother. Played by Wong You-nam.
* AnnoyingYoungerSibling
* CassandraTruth: Played with. While many of the people he told believed him when he said he saw Ip and Liu fighting, his brother didn't.
* TragicKeepsake: [[spoiler: A kite made by his brother.]]

!!Chow Ching-Chuen
A businessman who owns a cotton mill being plagued by Jin's bandits. His family flees to Hong Kong with Ip Man's family but he is shot in the head by a Japanese soldier. This causes him to forget his family and friends, thinking that everyone he sees is Japanese.
* EasyAmnesia: He is partially cured after hearing Ip Man beat Twister on the radio.
* TisOnlyABulletInTheBrain

!!Jin Shanzhao
A martial artist master from the north who came to Fo-shan. Played by Louis Fan.
* ArrogantKungFuGuy
* BadassLongcoat: Justified; it's cold up north.
* BloodKnight - Though more to prove his name than out of pure bloodlust, mind.
* DefeatMeansFriendship: Not in the first movie, mind you. But having the arrogance knocked out of him allowed him to find love and build a happy family by the second film, something he has come to thank Ip Man for.
* DotingParent: Having an adorable little girl is yet ''another'' incentive to turn away from a life of violence.
* EasilyForgiven: He had been involved in Ip's life three times in the first movie: first he challenged him to a duel and accidentally smashed up his house (and attacked Ip with a sword), then he had become a bandit and tried to beat and rob the factory Ip was helping at. Finally, he gave Ip's location to the Japanese who were hunting him. Yet when he reappears in the sequel, he's greeted as an old friend.
* HandwrapsOfAwesome: in the beginning of the first movie, he has his right hand wrapped up. Appropriately, his style is much more brutal and powerful than anyone he faces... until he reaches Ip Man.
* HeelFaceTurn
* HenpeckedHusband: Even though he accuses Ip Man of being one in the first film, he becomes one himself in the second.
* {{Jerkass}}: In the first movie.
* KarmaHoudini: See EasilyForgiven. He never pays for the various misdeeds of his youth.
* LoveRedeems: ''"Thank you for knocking some sense into me all those years ago. Now that I'm married, I'm a responsible man with a family now!!"''
* ProudWarriorRaceGuy
* SmugSnake: Also in the first movie.

!!Li Zhao
A police inspector in Fo-Shan. When the Japanese occupied China, he became a translator for them. Played by Lam Ka-tung.
* FaceHeelTurn / HeelFaceTurn: Did the former when the Japanese invaded by becoming a translator to them. Then did the latter when he started to secretly work against them while still being the translator, his notable moment being [[spoiler:[[KarmicDeath to turn]] [[SmugSnake Colonel Sato]]'s [[KarmicDeath gun against him and kill him with it]].]]
* LesCollaborateurs
* ReverseMole
* TheQuisling: Works rather closely with the Japanese BloodKnight Miura and Sato, however, [[SubvertedTrope subverted]] in that it's heavily implied he's doing it to protect his family.

!!General Miura
The Japanese general in Fo-Shan who was also a martial arts enthusiast. He often took Chinese martial artists to his building to fight against their Japanese counterparts. Played by Hiroyuki Ikeuchi.
* AntiVillain: He respects Chinese martial artists as brother warriors, and would rather have them be integrated into the Japanese Empire as such rather than killed as enemies.
* AuthorityEqualsAsskicking: He turned out to be much more of a skilled martial artist then the other Japanese ones.
* {{Badass}}: Gave Ip more of a challenge than ten of his men.
** BadassInCharge
** FourStarBadass
* BloodKnight: He was driven by his desire to pit the Chinese martial artists with the Japanese ones.
* BigBad: Of the first movie.
* DoesntLikeGuns: He forbids Sato from bringing a gun into his dojo, which he considers a place reserved for "martial spirit."
* HonorBeforeReason
* NobleDemon: Despite being the antagonist, he threatened to '''kill''' Sato for shooting Liu in the arena. He was also baffled when Lin would rather die against him than surrender.
* PiratesWhoDontDoAnything: Spends his time practicing karate and fighting local martial artists rather than anything you'd expect a general to actually do during a war.
* ProudWarriorRaceGuy: And an honorable one at that.
* ReasonableAuthorityFigure: Of an invading tyranny, yes, but he nevertheless treats the Chinese with as much dignity and respect as the Empire permits him to.
* {{Samurai}}: While nobody calls him this in the film, his dignified and noble behavior marks him as a likely descendent of a Warrior Clan.

!!Colonel Sato
Miura's right hand man. He was the more sadistic of the two. Played by Shibuya Tenma.
* ColonelBadass: Averted. While Sato is a colonel, he's too much of a cowardly SmugSnake to be this.
* TheDragon
* FourEyesZeroSoul
* [[spoiler: KarmicDeath]]: [[spoiler: He was shot by his own gun that he used to shoot Liu and Ip.]]
* SmugSnake
* WhyDontYaJustShootHim: He constantly tells Miura to just kill Ip.

[[folder:Introduced in ''Ip Man 2'']]
!!Wong Leung
Ip Man's first student in Hong Kong. Played by Huang Xiaoming.
* TheApprentice
* DefeatMeansFriendship: Doubly subverted. At first he rejects Ip's offer to be the man's student and came back with friends for another round. When he's conclusively shown the error of his ways, though, he gladly accepts the tutelage.
* HotBlooded

!! Hung Lei-Nan (Master Hung)
A Hung Ga master who started out as his enemy but later became his friend. Played by Sammo Hung.
* {{Acrofatic}}: A rather mild one but nonetheless he looked out of shape and yet managed to do acrobatic things to keep up with Ip.
* AFatherToHisMen: Master Hung's students are largely orphaned delinquents who are forced to turn to criminality to stay alive; by giving them a home along with his teachings, he gave them a second chance at life.
* {{Badass}}
** BadassGrandpa
** HandicappedBadass: Is able to fight Ip Man to a standstill in spite of being heavily afflicted with Asthma.
* CasualtyInTheRing
* EasilyForgiven: Introduced as the OpposingSportsTeam who basically tried to keep Ip from starting a kung fu school and got Ip arrested for rescuing his prize student. This changes after [[WorthyAdversary they fight to a draw]] and he [[EnemyMine faces off against Twister]].
* HonorBeforeReason: It is even {{lampshaded}} by Ip.
* NecessaryEvil: He is something of a {{Jerkass}} and OpposingSportsTeam to Ip Man early on, but it quickly becomes apparent that his rules, fees, and attitude are necessary for the martial arts schools to remain afloat under British rule.
* OldMaster
* OpposingSportsTeam: His initial role in the movie.
* ProudWarriorRaceGuy

A chief police superintendent in Hong Kong who called in protection fees from martial arts schools. Played by Charles Mayer.
* CorruptCop
* EvilBrit

!!Taylor "The Twister" Milos
A British boxer who came to fight in Hong Kong. Played by Darren Shahlavi.
* [[ArrogantKungFuGuy Arrogant Boxing Guy]]
* AxCrazy: Will happily kill his opponent if given an opportunity.
* BloodKnight
* BoxingBattler: In contrast with the kung fu the Chinese use, Twister sticks to boxing and manages to [[spoiler: beat Hung Lei-Nang to death]] and hold his own against Ip.
* TheBully
* EvilBrit
* ForTheEvulz: Does what he does for the sheer joy of humiliating his opponents.
* {{Jerkass}}
* LackOfEmpathy
* LightningBruiser: The Twister can take and dish it out well while still being fast enough to keep up with Master Hung and Ip.
* MeanCharacterNiceActor: Darren Shahlavi himself was a gracious, well spoken and polite Kung Fu practitioner, a polar opposite of the monster that is Twister.
* PoliticallyIncorrectVillain: He has a general distaste of Chinese martial arts and culture in general where he consistently mocked them.
* PutTheLaughterInSlaughter: Publicly and happily gloats that he's going to murder ''every'' Chinese warrior in Hong Kong in a rematch that is meant to clear his name.
* RedBaron: Twister
* TheSociopath
* ScrewTheRulesIHaveConnections: See ForTheEvulz for more details.
* VillainWithGoodPublicity: Due to his [[ScrewTheRulesIHaveConnections connections,]] the British audience seem to think of him as just a popular, skilled boxer. Given the way they cheer for Ip Man's speech at the end this may no longer be the case.

A Chinese police officer in Hong Kong who ensures that the martial arts clubs comply with the British police. Played by Kent Cheng.
* OnlyKnownByTheirNickname
* LesCollaborateurs: Like Li in the first film, Fatso is a policeman who reluctantly collaborates with the foreign occupiers before turning against them and helping the Chinese.
* ReverseMole

A young kid who wants to be (and [[ForegoneConclusion will be]]) Ip Man's student. Played by Jiang Daiyan.
* ForegoneConclusion: We all know what's going to happen to him...
* FutureBadass
* MouthyKid