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Luffy, inevitably, lost the first battle with Enel and had to fight him once again to beat him and save Skypiea.
6 Luffy Vs. Kuzan
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.
Luffy"s fight against Lucci is an iconic battle not only in One Piece but also in all of anime and manga. Although their fight at Enies Lobby is what everyone raves about, the two also clashed at Water 7, where Lucci ended up defeating him without much trouble.
On the way to Enies Lobby, however, Luffy developed Gear Second and Gear Third to keep up with CP-9 and rescue Robin from their 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 the Shichibukai Bartholomew Kuma. Sentomaru and his squad of Pacifistas were strong enough to completely overwhelm the crew.
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To make things worse for Luffy, his entire crew was blown away by Kuma, one of the Seven Warlords of the Sea. To date, it remains to be one of the biggest losses that the Straw Hat captain has ever suffered.
In an attempt to rescue his brother, Luffy broke into the greatest known prison in the world of One Piece, Impel Down. With Ace almost being within his reach, Luffy"s path was blocked by none other than the Warden of Impel Down, Magellan.
Thanks to his Doku Doku no Mi power, Magellan was able to defeat Luffy within moments as the latter stood absolutely no chance against him.
2 Luffy Vs. Katakuri (Round 1)
Just like other major battles, Luffy fought 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.
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 Yonko in Kuri, hitting him with everything that he had at once.
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Surprisingly, Kaido took the full brunt of the attacks and stood unfazed. In just one swing of his club, he knocked Luffy out and defeated him in the process.
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