Over the course of fourIp Manmovies, Donnie Yen’s character faced off with a multitude of formidable challengers. Some were close to home, while others were foreigners skilled in forms of fighting unfamiliar to Master Ip. Whether it was his own reputation that was attracting attention or someone else forcing Ip’s hand, he was constantly contending with fellow martial artists of varying skill levels and overcoming great challenges.
Some were beaten rather effortlessly, while others were strong enough to deliver some of theIp Manfranchise’s best fights. The latter, of course, generally stand out as among the most talented fighters intheIp Manmovies. Interestingly, though, it would seem that the strongest out of all his opponents was not even a main antagonist or someone who was included in the climax of a film.

Mike Tyson’s Frank Was The Strongest Rival To Ip Man
Frank And Ip Fought For 3 Minutes With No Decisive Winner
The timeline followed by the films provides evidence for the idea that Ip Man’s strongest opponent was Mike Tyson’s Frank, the American boxer he had a stalemate with inIp Man 3.Due to his advancing age over the course of the films,it’s impossible that Donnie Yen’s character’s prowess in battle was consistentfromIp MantoIp Man 4: The Finale’sending. After all, he went from 42 years old to 71 years old, plus he developed cancer. What’s worse is that Ip was just a year away fromhis death inIp Man 4.
Mike Tyson was 49 years old whenIp Man 3was filmed. It’s unclear exactly how old Frank was in in the movie.

Many of Master Ip’s opponents in those films (particularly the fourth installment) may have seemed especially challenging, but it’s important to note Ip’s health at the time. The fact that he gained decisive wins over the majority of his rivals - in spite of his physical decline - speaks volumes. However, this didn’t likely apply to his battle with Frank, as he was also not in his prime and was similarly depicted as an aging fighter. So unlike mostIp Manvillains,Frank fought Ip without a massive age advantage- and didn’t lose.
Ip Man’s Age Makes Two Ip Man Villains Look Weaker
The Villains Of Ip Man 3 & Ip Man 4 Weren’t Close To Ip’s Skill Level
Evidently,Frank was a better fighter than the main villains of bothIp Man 3andIp Man 4.Whereas Frank tied with Ip inIp Man 3, Zhang Jin’s Cheung Tin-chi suffered a clear defeat. The same was the case for Scott Adkins' Geddes in the fourthIp Manmovie, but by this point, Ip was in his 70s and in terribly poor health. The fact that Geddes (or any of the fighters inIp Man 4) couldn’t beat him in such a state is indicative of the idea that Ip had already dealt with his strongest challengers.
Ip Man: What The Martial Arts Movies Omitted About Bruce Lee (& Why)
The Ip Man movies left out a major element of Bruce Lee’s life, but this ended up being for the best, both for the series and Lee’s role in it.
Rather than theIp Manvillains' skill level increasing as the story progressed from movie to movie, there’s a sense that the quality of his opponents actually decreased afterIp Man 2. With his raw power, Taylor “Twister” Miller truly was a force to be reckoned with, but still one that Ip eventually overwhelmed with an indisputable victory. With the exception of Frank, he was seemingly handed much weaker rivals to fight after that, with his age and health being the main source of the adversity he faced.

Ip Man 3
Cast
In post-war Hong Kong, legendary Wing Chun master Ip Man is drawn into a conflict when a brutal gang led by a crooked property developer targets his son’s school. Balancing family commitments and the challenges of a new rival, Ip Man’s journey will once again test his resolve.
