Monkey D. Luffy is the main protagonist of Eiichiro Oda’s One Piece series, and he set out to sea with the aim of becoming the King of the Pirates. Having eaten the Gum-Gum Fruit, Luffy’s battle prowess has grown tremendously and with more training, he’s become one of the strongest in the series.
Luffy is far from unbeatable, however, and there are actually many One Piece villains who beat Luffy once or even twice until the Straw Hat pirates triumphed in the end. In fact, most One Piece story arcs involve at least one fight where Luffy either was forced to retreat or was outright defeated, and that adds suspense while also making the villain that much more impressive.
Update on August 19th, 2023 by Louis Kemner: How many times has Luffy lost a fight in One Piecer? He always wins when it matters most, but in between Luffy’s iconic victories over villains like Crocodile and Doflamingo, he’s liable to get in over his head and take a beating from hostile pirates and Marine officers. This post has been updated to meet CBR’s current formatting standards, as well as to showcase new images.
10 Luffy Vs. Higuma the Bear
Luffy’s very first fight in One Piece was a short one, since Luffy was just a young boy and hadn’t yet started training with his new Gum-Gum powers. When Red-Haired Shanks visited Luffy’s hometown, a minor bandit lord named Higuma decided to bully everyone, and Shanks took the high road by ignoring him at first.
When Luffy confronted this villain, Higuma quickly had Luffy defeated, and even tried to kill the boy. Fortunately, a sea monster at Higuma, and once Luffy ended up in the water, Shanks arrived to rescue him, at the cost of an arm. Higuma may be the first villain who defeated Luffy, but he didn’t have long to boast about it.
9 Luffy Vs. Captain Smoker
Luffy’s first proper defeat in One Piece came at the hands of Captain (now Commodore) Smoker, who served as a Marine officer back during the Logue Town arc. Being a Logia type made of smoke, it was impossible for Luffy to beat Smoker with physical attacks without the benefit of Color of Arms Haki.
The battle between the two wrapped up quite quickly and ended in favor of Smoker. Ultimately, Luffy needed to be saved and his father, Monkey D. Dragon, stepped in to save him instead. Luffy seized that opportunity to flee Loguetown, and he and his crew set sail in a rainstorm for the Grand Line, leaving Smoker and Tashigi far behind.
8 Luffy Vs. Sir Crocodile
Luffy’s first big challenge in the Grand Line came against one of the Seven Warlords of the Sea and the leader of Baroque Works, Sir Crocodile. As a pirate, Crocodile was known to be ferocious, having sailed the seas of the New World in the past, and he showed Luffy no mercy.
With his Sand-Sand Fruit powers, he was a tremendous enemy for Luffy, and he is one of the few villains who defeated Luffy more than once, although the third battle ended in Luffy’s favor. Nonetheless, Crocodile gave Luffy his first taste of what Grand Line is like, and Luffy nearly died in the process.
7 Luffy Vs. Enel
Luffy and the self-proclaimed Enel traded blows with each other during the Skypiea arc of One Piece when they met in the Upper Yard, the Land of God. Thanks to his rubber Devil Fruit, Luffy was able to withstand most of Enel’s attacks; however, the skill of the latter was still levels above him.
Luffy, inevitably, lost the first battle with Enel and had to fight him once again to beat him and save Skypiea. Even with the benefit of lightning immunity as a rubber warrior, Luffy was in for the fight of a lifetime, and he had to tread carefully around a villain who defeated Luffy once before.
6 Luffy Vs. Kuzan/Admiral Aokiji
Prior to the Water 7 arc of One Piece, Luffy and the Straw Hat Pirates crossed paths with Kuzan, an Admiral of the Navy. With him being an Admiral, there was only one winner in the fight, and Luffy, even with help from Zoro and Sanji, stood absolutely no chance.
Although the crew lost badly, Kuzan spared them. Luffy ended up getting stronger, as a result, to make sure he had the strength to protect those close to him. At the time, Kuzan was a benign antagonist whom Luffy had to carefully avoid, but in more recent One Piece arcs, Kuzan is a member of the Blackbeard pirates, making him a deadly foe for Luffy and the Navy.
5 Luffy Vs. Lucci (Water 7)
Luffy’s fight against Lucci is an iconic battle not only in One Piece but also in all the anime and manga. Although their fight at Enies Lobby is their most definitive battle, the two of them also clashed at Water 7, where Lucci ended up defeating him without much trouble.
On the way to Enies Lobby, however, Luffy developed Gear 2 and Gear 3 to keep up with CP9’s formidable power and rescue his kuudere shipmate Nico Robin from the Navy’s grasp. As always, Luffy learned quite a lot from his fight against Lucci.
4 Luffy Vs. Sentomaru And Pacifistas
At Sabaody Archipelago, the entire Straw Hat crew was utterly defeated by a joint force of the Navy and one of the Warlords of the Sea, Bartholomew Kuma himself. Sentomaru and his squad of Pacifistas were strong enough to completely overwhelm the crew, too, even if they had less diversity in their powers.
To make things worse for Luffy, his entire crew was blown away by Kuma and the power of his Paw-Paw Fruit. To date, it remains to be one of the biggest losses that the Straw Hat captain has ever suffered, and it took quite some time for the Straw Hats to reunite for further adventures in the New World.
3 Luffy Vs. Warden Magellan
In an attempt to rescue his foster brother Ace, Luffy broke into the greatest known prison in the world of One Piece, Impel Down. He reached that prison’s hellish fourth floor by the time warden Magellan himself caught up to Luffy, and they fought a short but vicious battle there.
Luffy stood little chance against Magellan’s Venom-Venom Fruit, which soon had Luffy writhing in agony, dying from deadly toxins. Magellan showed a little mercy after he saw Luffy defeated, and sent Luffy to level 5 rather than just kill him outright, giving Mr. 2 and Ivankov one last chance to save the Straw Hat hero’s life.
2 Luffy Vs. Charlotte Katakuri (Round 1)
Just like other major battles, Luffy fought Charlotte Katakuri a couple of times before he actually managed to get on his level and defeat him in combat. The two clashed at the Tea Party first, where Luffy needed saving from Jimbei.
Later, in the Mirroworld, Luffy and Katakuri fought again and the Sweet Commander proved his superiority over the Straw Hat captain, forcing him to abandon the fight until his Haki returned. In the final battle, however, Luffy triumphed with the superior use of Haki, though it was still a close fight.
1 Luffy Vs. Kaido
Monkey D. Luffy went head-to-head against one of the Four Emperors of the Sea, Kaido, in the Wano Country arc of One Piece. Although the plan was to take Kaido down at Onigashima, Luffy first engaged the Emperor in Kuri, hitting him with everything that he had at once.
However, Kaido took the full brunt of the attacks and stood unfazed. With just one swing of his club, Kaido knocked Luffy out and defeated him with casual ease, allowing him to join the ranks of One Piece villains who beat Luffy before finally facing his own defeat later on.