Wing Chun master Ip Man (Donnie Yen) had many notable fights throughout the Ip Man series, frequently fighting off multiple men and enemies who towered over him. While none of his opponents were able to best him, here's the challengers who put Bruce Lee's mentor through his hardest fights.
Colin Frater (Ip Man 4)
Marine karate instructor Colin Frater (Chris Collins) was able to best several martial arts instructors, but he was easily overwhelmed by a septuagenarian Ip. While Frater was capable of delivering powerful strikes, none of the killer shots landed on the martial arts legend. To make matters worse, Ip was diagnosed with throat cancer at the beginning of the movie, meaning he wasn't at his peak when he swiftly took down Frater. If one of the Marine Corps' best fighters can't take down an ailing cancer patient in their 70s, the branch's entire hand-to-hand combat program needs an overhaul.
General Miura (Ip Man)
Although General Miura (Hiroyuki Ikeuchi) was the final opponent in the first Ip Man, it's easy to see why his colonel had to threaten the martial arts master. It's almost unfair to call this showdown a fight, as Miura was virtually defenseless against Ip's multitude of strikes. Ip's anger toward the occupation of Foshan didn't do Miura any favors either, as the Wing Chun legend had nothing to lose. While the general wasn't much of an opponent, this fight is a perfect example of Ip in his top form, with his Wing Chun flowing beautifully throughout the duel.
Suchart (Ip Man 3)
Suchart (Simon Kuke) has one of the smaller roles in Ip Man 3, but his elevator fight with Ip was one of the best combat sequences in the entire series. Unfortunately, a cool showdown doesn't make Suchart one of Ip's tougher opponents, especially when the Muay Thai fighter failed to catch him off guard. While Muay Thai is certainly lethal, it's not a good idea to fight a Wing Chun Master in a tight space, especially when their fighting style thrives on close contact. While Suchart had the physical capabilities to fight Ip, he was mentally unprepared for their battle.
Wan Zhong-Hua (Ip Man 4)
Grandmaster Wan Zhong-Hua (Wu Yue) was the first opponent to take on Ip during his fourth film, with the two closing out the fight in an impressive one-handed Tai Chi versus Wing Chun showdown. The choreography in this sequence is majestic, as both opponents push their fighting skills beyond conflict into an art form. Both fighters also demonstrate a great amount of patience and intellect, as they each strike with caution while keeping their defenses up. Although the fight officially ended in a standstill, Zhong-Hua was eventually defeated by Barton Geddes (see below), knocking down his ranking.
Jin Shan Zhao (Ip Man)
Jin Shan Zhao (Louis Fan) made easy work out of Foshan's toughest Nanquan fighters, but his aggressive Northern kung fu was no match for Ip's calm counters. Zhao's acrobatics and athleticism are both impressive, but the fighter wasn't capable of defending himself at all. The fact that Zhao lost a sword fight against a simple feather also cements the fact that he was outmatched. While Ip asserts that fighters, not styles, determine the outcome of a fight, his pure defensive capabilities definitely helped him come out on top.
Barton Geddes (Ip Man 4)
Marine Corps Gunnery Sergeant Barton Geddes (Scott Adkins) was Ip's final fight in the series and he almost came out on top. By the time of their matchup, Geddes proved himself to be an effective fighter by taking down Zhong-Hua, who kept Ip at a standstill. At the same time, Ip was nowhere near his top form by this film, clearly suffering from the effects of throat cancer and old age. The duo's brutal karate verses Wing Chun showdown was tense, but it's hard to disregard the fact that Ip still won despite his huge physical disadvantages.
Hung Chun-nam (Ip Man 2)
Ip Man 2's showdown between Hung Chun-nam (Sammo Hung) and Ip on a rotating table is another iconic moment from the series, complete with stunning cinematography and impressive footwork. Ip's takedown of all of the Hong Kong masters was already impressive on its own, but his fight with Chun-nam pitted him against an opponent who was almost his equal. While Chun-nam was an expert Hung Ga master, he suffered from asthma, which led to his eventual death at the hands of Taylor "The Twister" Miller. It's interesting to think about what would've happened if both masters duked it out in their prime.
Taylor "The Twister" Miller (Ip Man 2)
The final match between Ip and Taylor "The Twister" Miller (Darren Shahlavi) in Ip Man 2 was loaded with handicaps against the Wing Chun master, who was forced to stop using his legs in the final round. To make matters worse, The Twister was also larger than Ip, giving him a better reach and a significant physical advantages as a boxer. These factors nearly rigged the fight in the Twister's favor, but Ip still proved himself to be the better fighter, cementing the fact that style doesn't matter.
Frank (Ip Man 3)
Although Frank's (Mike Tyson) showdown was one of the more ridiculous fights in Ip Man 3, it was also one of Ip's most difficult. It's amazing to see how Ip was able to avoid and counter Frank's massive blows, despite the American business man's age. If Tyson's recent fight against Roy Jones Jr. proved anything, it's that the man is still in top fighting form at the age of 54. This make's Ip's stalemate even more impressive — if he can withstand three-minutes in the ring with one of the greatest heavyweights of all time, he can take on anyone.
Cheung Tin-chi (Ip Man 3)
This Wing Chun versus Wing Chun battle between two masters is easily the best fight in the entire series and Ip's toughest battle to date. Both combatants were in top form, switching off between punches, kicks and weapons throughout their lengthy battle. The multiple back-and-forths between Cheung Tin-chi's (Zhang Jin) strikes and counters against Ip's are thrilling from start to finish, with both actors engaged in fluid choreography throughout. It also served as the series' introduction to the legendary one-inch punch, which closed out the film on a high note.