Ip Man’s Toughest Opponents, Ranked

Ip Man's Toughest Opponents, Ranked

Ip Man has fought some fierce opponents throughout his film, but there are some that are more ferocious than the rest. Wing Chun master Ip Man (Donnie Yen) fought many notable fights throughout the Ip Man series, often fighting multiple men and enemies who towered over him. While none of his opponents were able to best him, here are the contenders who put Bruce Lee’s mentor through his toughest fights.

Colin Frater ( Ip Man 4)

Marine karate instructor Colin Frater (Chris Collins) was able to best several martial arts instructors, but was easily defeated by septuagenarian Eep. Although Frater was capable of delivering powerful blows, none of the killing shots hit the martial arts legend. To make matters worse, Yip was diagnosed with throat cancer at the beginning of the film, meaning he wasn’t at the peak of his career when he quickly defeated Frater. If one of the Marine Corps’ best fighters can’t defeat a 70-year-old man with cancer, the unit’s entire hand-to-hand combat program will need 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.

Ip Man Villain Who Would Have Suited Donnie Yen

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 Wang Zhong-Hua (Wu Yue) was the first opponent to fight Ip during his fourth film, and the two finished the fight with an impressive one-handed Tai Chi match against Wing Chun. The choreography in this episode is majestic as both opponents take their fighting skills beyond conflict into an art form. Both fighters also show great patience and intelligence as they each strike carefully while maintaining their guard. Although the fight officially ended in a stalemate, Zhong-Hua was ultimately defeated by Barton Geddes (see below), lowering 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 Eep’s last fight on the show, and he almost emerged victorious. By the time of their match, Geddes had proven himself to be an effective fighter, defeating Zhong-Hua, who had Yip at a stalemate. At the same time, in this film, Eep was far from his best, clearly suffering from the effects of throat cancer and old age. The duo’s brutal Wing Chun karate bout was intense, but it’s hard to ignore the fact that Eep still won despite his enormous physical limitations.

Top 10 Behind The Scenes Secrets Of The Ip Man Franchise

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)

While Frank’s (Mike Tyson) fight was one of the most ridiculous fights in Ip Man 3, it was also one of the toughest fights for Ip. It’s amazing to see how Eep was able to avoid and parry Frank’s powerful blows, despite the American businessman’s age. If Tyson’s recent fight against Roy Jones Jr. proved anything, it’s that at 54 years old, the man is still in excellent fighting shape. This makes Yip’s stalemate even more impressive – if he can handle three minutes in the ring with one of the greatest heavyweights of all time, he can fight 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.