This list contains spoilers for One Piece.

Monkey D. Luffy is one of the strongest characters that fans have seen in One Piece over the years. He is a powerful pirate who has gone from strength to strength and has currently attained the status of a Yonko. While Luffy is almost unbeatable at this point in time, that certainly does not mean he has not been defeated in the past.

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In fact, on his journey as a pirate, many other powerful pirates have encountered him and actually went on to defeat him in battle. Although these pirates are very rare and quite special in their own ways, they have certainly done a number on the Straw Hat pirate.

Sir Crocodile

Crocodile is one of the first pirates to actually defeat Luffy. Crocodile was the first proper enemy that Luffy faced in the Grand Line, and it is safe to say that he lived up to the expectations. Up until then, all of Luffy's enemies were easy for him to beat. Crocodile broke the tradition and left Luffy for dead not once but twice. The first time they fought in a desert was when Crocodile showcased the Massive gulf in their skills to the Straw Hat pirate.

He ended up defeating Luffy effortlessly before the time he allotted for the battle was up. Later on, Crocodile once again went on to defeat Luffy, this time, by sucking all the moisture from his body. Luffy survived by pure luck, and went on to defeat him in their third fight. However, for two rounds straight, Crocodile defeated Luffy again and again.

Bartholomew Kuma

kuma defeats luffy and the straw hat pirates one piece

In the Sabaody Archipelago arc, the Straw Hat Pirates were absolutely decimated, and much of that was down to Bartholomew Kuma. Fans know him to be an incredibly powerful pirate who was actually strong enough to take out the entirety of the Straw Hat crew back then. Kuma utilized the power of his Nikyu Nikyu no Mi to separate the Straw Hats. Even though he was trying to save them, this was clearly a defeat for the Straw Hats at his hands, and something that went on to traumatize them for quite a while.

Big Mom's Enraged Army

big mom's enraged army defeated luffy in one piece

In the Whole Cake Island arc of One Piece, fans got to see Luffy lose to an army of powerful fighters. Big Mom's Enraged Army was called into action after the defeat of Charlotte Cracker, and they showed Luffy no mercy. Clearly, this was not a fair battle by any means. Luffy was fighting 10,000 pirates on his own, all of whom had incredibly high bounties.

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At the same time, at this point, Luffy could not fight or defeat them on his own since he was exhausted. However, he still fought as well as he could. Eventually, however, he was crushed by the army and locked away in the Book Prison by Mont d’Or.

Big Mom

In the Whole Cake Island arc of One Piece, Luffy and Big Mom did not get to have a proper fight, and all they had was a skirmish. This skirmish was enough to see the Yonko win. Luffy jumped at the Yonko in an attempt to clash with her, and when he did so, Big Mom effortlessly blocked his attacks with her arm and proceeded to overwhelm him.

Luffy lost all his gas and needed to be carried by Sanji. Of course, this is not a clear and proper defeat for the Straw Hat pirate, but it is certainly one of his smaller defeats. Luffy essentially lost all power here. Had Sanji not been there, he would have died right there. Unfortunately, Luffy and Big Mom never got to have a proper battle and fans would have absolutely relished this clash in the series. Hopefully, if Big Mom is alive, these two can have another bout later down the line.

Kaido

kaido was luffy's hardest fight one piece

Of course, the pirate who gave Luffy his worst defeat in One Piece is certainly Kaido. The first time they fought in Kuri saw Luffy being utterly outclassed and destroyed in battle. A single swing from Kaido was enough to knock him out completely. After Luffy's many power-ups, they fought again on the rooftop of Onigashima, and Luffy lost to him two more times, being knocked out in both encounters.

Eventually, Luffy did triumph over Kaido, but this victory came only after learning from his many defeats. Kaido has defeated Luffy the most times in One Piece so far. The first time he did so, he used Raimei Hakke to beat him. Kaido used Raganaraku to knock him out the second time. The third time, he was knocked down from the roof of Onigashima and was saved from the ocean by the Heart Pirates. In fact, Luffy then went on to lose again to Kaido, and this time, he actually lost his life as well in the process. However, after he fell, he essentially gained greater power which he then utilized to defeat the Yonko.

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Release Date
October 20, 1999
Network
Fuji TV
Directors
Hiroaki Miyamoto, Konosuke Uda, Junji Shimizu, Satoshi Itō, Munehisa Sakai, Katsumi Tokoro, Yutaka Nakajima, Yoshihiro Ueda, Kenichi Takeshita, Yoko Ikeda, Ryota Nakamura, Hiroyuki Kakudou, Takahiro Imamura, Toshihiro Maeya, Yûji Endô, Nozomu Shishido, Hidehiko Kadota, Sumio Watanabe, Harume Kosaka, Yasuhiro Tanabe, Yukihiko Nakao, Keisuke Onishi, Junichi Fujise, Hiroyuki Satou
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  • Cast Placeholder Image
    Mayumi Tanaka
    Monkey D. Luffy (voice)
  • Cast Placeholder Image
    Kazuya Nakai
    Roronoa Zoro (voice)

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One Piece is a Japanese manga written and illustrated by Eiichiro Oda. The series follows protagonist Monkey D. Luffy and his Straw Hat Pirate crew as they explore the Grand Line to find the King of the Pirates' ultimate treasure, the One Piece, in order to become the next king. The manga's popularity helped it spin off into a larger media franchise, including an anime with more than 1,000 episodes.

Studio
Toei Animation
Creator
Eiichiro Oda
Streaming Service(s)
Crunchyroll, Netflix, Hulu, Pluto TV