Luffy has faced some incredibly strong opponents throughout his adventure. These were the toughest opponents he’s ever faced.

HIGHLIGHTS

 Luffy has faced tough opponents, from Kuro to Kaido, each pushing him to his limits and making him stronger.
 Battles against foes like Don Krieg and Gecko Moria forced Luffy to use his various powers and strategies to win.
 Fights against allies like Usopp and Sanji were emotionally challenging, showcasing the depth of Luffy’s relationships.

Monkey D. Luffy is the protagonist of Eiichiro Oda’s One Piece series. Intending to become the Pirate King, Luffy set out to sea in an era where pirates are on the rise. To attain this title, Luffy has had to become stronger with every obstacle that he’s faced.

Haki has takes several different forms in One Piece, each of which has unique applications. Here’s all the ways this mysterious force can be utilized.

Over the years, Monkey D. Luffy has gained several new powers as he crushed his enemies and right now, he’s one of the strongest people in the entire One Piece world. His journey certainly hasn’t been easy, however, and he has struggled against quite a few opponents so far.

Updated on February 24, 2024, by Rei Penber: Luffy has come incredibly far over the years, thanks to the many battles that he has fought and won. Recently, after the events of Wano, he was made one of the Emperors of the Sea and that just goes to show the level that he is on right now. However, Luffy is still far from the finished product and, as a result, he is still engaging in many high-level battles. While this list already goes over the vast majority of the toughest Luffy fights, there are others that have managed to push him to his limits, especially now in the final saga of the story. As a result, this list of the toughest Luffy fights has now been updated.

Note: This list doesn’t indicate the strength of his opponents, but rather the difficulty of the fights he fought.

22Kuro

Fight Begins: Episode 15

Luffy’s fight against Kuro was quite a challenge for him, especially when it came to dealing with the incredible speed the latter possessed. While Luffy was successful in landing quite a few hits on him in their fight, once Kuro tapped into the power of the Nuki Ashi technique, it became difficult for him to overcome the obstacle.

After taking quite a few hits from him and getting used to his speed, Luffy was eventually able to predict his movement pattern and counter effectively. While Kuro might not be the hardest fight he’s fought, he’s certainly one who gave him a lot of trouble quite early into the series.

21Don Krieg

Fight Begins: Episode 27

Don Krieg was the captain of the Krieg Pirates and commanded the Krieg Armada, the biggest known force from the East Blue. During the Baratie arc, Krieg fought against Luffy in an enthralling battle and fared quite well.

One Piece should focus on these characters after Egghead Island concludes.

Although not the strongest, he possessed an arsenal of weapons that made him quite dangerous. Don Krieg had access to an overpowered battle spear that gave Luffy quite a tough time, along with the MH5 gas. Although Luffy won this fight, it required every bit of his energy to overcome Krieg.

20Gecko Moria

Fight Begins: Episode 372

Gecko Moria was the main antagonist of the Thriller Bark arc and one with a bounty of 320 million berries which, at the time, surpassed even Luffy’s own. Moria was quite a troublesome opponent for Luffy to deal with. During their fight, he made clever use of techniques such as Brick Bat to keep Luffy engaged.

At his strongest, even Gear Second wasn’t enough to defeat him so Luffy had to combine Gear Second with Gear Third for the very first time. At the expense of his life force, Luffy was ultimately able to take Moria down but not before passing out from exhaustion himself.

19Enel

Fight Begins: Episode 182

The God of Skypiea, Enel was the main antagonist of One Piece’s Skypiea arc. With the power of the Goro Goro no Mi, he was practically invincible against everyone there, except for Luffy, who could resist his lightning powers due to his Gomu Gomu no Mi powers.

Despite being at a clear disadvantage, Enel was able to defeat Luffy once. His mantra, along with his tactical prowess in battle made him quite a foe for anyone. In the end, Luffy had to seek help from all those around him to take Enel down.

18Luffy Vs. Usopp

Fight Begins: Episode 236

Luffy fought against Usopp in the Water 7 arc when the idea of replacing Merry came up. The Merry was an incredibly wonderful ship that had journeyed with the Straw Hat Pirates all the way from the East Blue to the Grand Line. However, she was reaching the end of her days and Luffy realized that, even though he wanted his best to help her. Usopp, for many reasons, did not understand this as simply and decided to leave the crew. He challenged Luffy for possession of the Merry and eventually, the two fought.

Zoro will surpass these powerful swordsmen in the final saga of One Piece.

Usopp Made Luffy’s fight against him quite difficult, however, Luffy ended up winning in the end. That said, this fight was probably hard for Luffy not only because Usopp posed a great challenge, but also because it was one of his best friends who he was fighting. The emotional weight that he had to carry made it one of the most difficult fights that Luffy has ever engaged in One Piece.

17Luffy Vs S-Bear

Fight Begins: Chapter 1075

In the Egghead Island arc, Luffy also fought against one of the Seraphims, S-Bear, who fans know to be the clone of Bartholomew Kuma. S-Bear is quite a powerful Seraphim with the power of the Nikyu Nikyu no Mi, and, at the same time, he has also been infused with the Lunarian Lineage Factor. On top of that, his body is that of an improved Pacifista, and all these combinations make him the pinnacle of science in the One Piece world.

S-Bear is so strong that even Luffy couldn’t damage him with his attacks. Of course, this fight was an extended one where Luffy was getting tired after hitting him again and again and S-Bear simply absorbed all of them since the flames on his back were on all the time. Sadly, fans did not get to see how this fight concluded. All they know is that at the end of it, S-Bear was trapped inside a bubble somehow. Fans can assume that Luffy played a significant part in that and, thus, could have won this clash.

16Luffy Vs. Lucci (Rematch)

Fight Begins: Chapter 1069

Luffy and Rob Lucci have quite a great rivalry with each other. Fans have enjoyed this rivalry since the days of the Water 7 arc and it has only grown more intense since. In the Final Saga One Piece, Luffy and Lucci met once again. On Egghead, Luffy was sent to assassinate Vegapunk and Luffy landed there by sheer luck. The two immediately went on to fight again. Both Luffy and Lucci were desperate to fight against each other and they immediately took their new forms.

Luffy tapped into the power of Gear 5, while Lucci showed his Awakened state to the fans. While this fight wasn’t too hard for Luffy, Lucci certainly proved to be difficult. One of his greatest assets was his recovery rate, which saw him get up again and again even after being knocked down by the future Pirate King. At the end of the fight, Luffy was left looking like an old man due to the strain that Gear 5th puts on his body.

15Luffy Vs Don Chinjao

Fight Begins: Episode 646

Luffy fought against Don Chinjao, a legendary pirate worth 542 million berries, during the Dressrosa arc of One Piece. In the Corrida Colosseum, where the hunt for the Mera Mera no Mi was going on, Luffy fought a significant battle against this legendary pirate. This fight was incredibly intense and forced Luffy to push himself to use both Gear Second, and Gear Third, and utilize his Haki to the very maximum.

In the end, Luffy was able to beat him by using a powerful technique that restored the drill on his head. Chinjao then ended up becoming a loyal follower of Luffy and, currently, he is a member of the Straw Hat Grand Fleet as well.

14Luffy Vs Kizaru

Fight Begins: Chapter 1091

Luffy and Kizaru first met during the Sabaody Archipelago Arc, however, their proper fight only happened much later in the story, on Egghead. By this point, Luffy was already declared one of the Emperors of the Sea, and, as a result, for Kizaru, this battle was an uphill task. Even though Luffy wasn’t going all out and was already carrying several injuries before the fight even began, he was still in the driving seat.

Despite that, Luffy successfully completed his mission at the end of the fight, as he was easily able to knock him down permanently. He generated so much force that Kizaru couldn’t even sit up. While Luffy himself ended up burning all his stamina, his victory over Kizaru was absolutely resounding. Furthermore, it must also be noted that Luffy accomplished this without even pushing himself to his absolute maximum.

13Sentomaru

Fight Begins: Episode 403

Sentomaru made his One Piece debut during the Sabaody Archipelago where he fought Luffy and managed to cause him all sorts of trouble. With incredible defense and a Haki that was especially strong, Sentomaru was able to take the brunt of the force that Luffy threw his way and counter effectively.

Sanji will surpass these characters in the final saga of One Piece.

With his Ryuo, he could damage Luffy quite severely and, for the first time, make him consider running away from a battle. Sentomaru might not have given fans the flashiest of battles but he certainly gave fans one that saw Luffy struggle quite a lot.

12Pacifista

Fight Begins: Episode 401

On Sabaody Archipelago, the Straw Hat Pirates were introduced to the Pacifistas for the very first time. Surprisingly, it took the combined effort of the entire crew to fight them. Luffy, who played quite a big role in the battle, wasn’t able to defeat any of them by himself.

Eventually, the crew managed to defeat the Pacifista but not before Luffy was exhausted after repeatedly using Gear Second and Gear Third. Without a doubt, the Pacifista caused all sorts of trouble for him in battle.

11Donquixote Doflamingo

Fight Begins: Episode 721

Also known as the Heavenly Demon, Donquixote Doflamingo was the main antagonist of One Piece’s Dressrosa arc. Being a Shichibukai, Doflamingo was quite difficult to take down in battle and he held the upper hand in the fight against Luffy for the longest time.

However, once Luffy went Gear Fourth, Doflamingo was absolutely no match for him. Even then, Luffy’s lack of energy made this fight even harder for him as he needed ten minutes to regain his Haki and thus, survive. By using his strongest attack, Luffy was ultimately able to defeat him.

10Charlotte Cracker

Fight Begins: Episode 798

Charlotte Cracker is one of the Three Sweet Commanders of the Big Mom Pirates and has a bounty of 860 million berries on his head. Cracker was incredibly difficult for Luffy to fight as his Armament Haki was quite powerful.

Zoan Devil Fruits give their users some amazing abilities. These are the strongest ones showcased so far.

Just one biscuit soldier created by Cracker required him to go Gear Fourth, which just goes to show how strong he was. Even when Luffy used Gear Fourth multiple times, he couldn’t defeat Cracker in combat. It was only when Nami helped him that he was finally able to take down the Sweet Commander.

9Luffy Vs Smoker

Fight Begins: Episode 53

Luffy has fought against Smoker on many occasions, however, the most difficult battle for him against this marine adversary was in Loguetown, when they first met. At this point, Smoker was a Marine Captain, and he had a record of not letting any pirate pass through Loguetown.

Smoker fought Luffy and with the power of his Moko Moku no Mi, he was able to restrain him. Smoker would have arrested Luffy had it not been for Dragon. This is a battle that Luffy lost despite trying his very best in the fight.

8Luffy Vs. Sanji

Fight Begins: Episode 807

Luffy’s fight against Sanji is quite similar to the one he fought against Usopp, in the sense that it carried an incredible emotional weight for him that was too much to bear. When Luffy reached Whole Cake Island, he wanted to retrieve Sanji, however, the latter realized that if he did not agree to what Big Mom and his family wanted from him, they would kill not just the Straw Hat Pirates’ loved ones, but also Zeff.

With that fear in mind, Sanji decided to stay behind. When Luffy came to get him, Sanji fought him and told him that he was only pretending to be a part of the crew. Luffy saw right through him and when Sanji attacked him, Luffy did not fight back. Eventually, Sanji knocked him out, however, even then, Luffy saw through his facade, telling him that he would wait for him and eat nobody else’s food. Sanji eventually returned to Luffy, however, this encounter will forever be remembered as one of Luffy’s most difficult fights. Not only was it difficult for Luffy to take on Sanji in combat but the fact that they are best friends made it even harder. Both Sanji and Luffy were suffering at the end of this fight. However, the reconciliation they had later made things even better.

7Luffy Vs Enraged Army

Fight Begins: Episode 811

In the Whole Cake Island arc, Luffy had many battles to fight and one of the most significant ones came against the Enraged Army of the Big Mom Pirates. After Luffy defeated Commander Cracker, Big Mom sent her children as a part of the Enraged Army to crush him.

By this time, Luffy was already tired, especially since he was defeated by Sanji. He was then pummeled by the Enraged Army until he passed out completely. Luffy lost this fight terribly and was then captured by Mont d’Or in his book world.

6The Three Admirals

Fight Begins: Episode 474

Luffy fought the Three Admirals during the Marineford arc of One Piece and was obviously no match for them. However, he had no choice but to fight them or Ace would’ve died.

The Admirals didn’t take him seriously and didn’t even use their full powers against him. Luffy was subdued pretty quickly but was always saved by those around him, such as Marco, allowing him to escape from them every single time.

5Charlotte Katakuri

Fight Begins: Episode 852

Katakuri was the strongest of the Three Sweet Commanders of the Big Mom Pirates and he fought Luffy towards the end of the arc. The two engaged in a gruesome battle in the Mirro World where Katakuri absolutely dominated Luffy.

Surprisingly, Luffy picked up the ability to see the future during this fight and thus leveled the field. After taking quite a beating for twelve hours, Luffy finally went all-out using Gear Fourth: Snakeman and defeated the strongest opponent that he had faced at that point.

4Sir Crocodile

Fight Begins: Episode 110

Sir Crocodile was the main antagonist of the Alabasta arc of the series and the first Shichibukai that Luffy took down. Crocodile is easily one of the most difficult fights that Luffy has ever fought as he lost to him twice.

These characters will be surpassed by Luffy in One Piece’s final saga.

In fact, Luffy would’ve died both the times had luck not been on his side. He was saved from a near-death state by Nico Robin outside of Rain Dinners and later, by his sheer luck in Alubarna. Even during their last fight, Crocodile poisoned him heavily and Luffy was on his very last legs throughout the battle.

3Rob Lucci

Fight Begins: Episode 294

The main antagonist of the Enies Lobby arc, Rob Lucci was quite a challenge for Luffy. The two clashed initially in Water Seven and the Straw Hat captain was completely outclassed by him in combat.

In Enies Lobby, Lucci once again held the upper hand even when Luffy gained two new powers in the form of Gear Second and Gear Third. Eventually, it was the motivation to save Robin that pushed Luffy beyond his limits and allowed him to defeat Lucci.

2Magellan

Fight Begins: Episode 435

Magellan is the Vice-Warden of Impel Down and before the time skip, he held the position of the Warden. He clashed against Luffy in the fourth level of Impel Down, known as the Burning Hell.

Magellan was way stronger than Luffy and was able to easily overpower him in battle. Although Luffy managed to bring him to his knees, he was unable to take him down and ended up almost dying in the fight.

1Luffy Vs. Kaido

Fight Begins: Episode 914

Luffy Vs. Kaido is one of the best fights that fans have seen in One Piece over the years, if not the best. The fight is, undoubtedly, the most difficult one that Luffy has fought so far. Kaido managed to defeat Luffy three times. For the first time, Luffy faced defeat against him Kuri and was thrown in prison. There, he learned Internal Destruction Ryuo and took Kaido on during the Onigashima Raid. Much to the surprise of the fans, Luffy lost again and when he got up and realized that he could use Conqueror’s Haki in battle, he attempted to fight Kaido but lost once again.

When Luffy got up, his control over his powers had grown significantly and he tried to take on Kaido one more time. Much to the surprise of the fans, CP0 interfered in that fight and Luffy ended up at the receiving end of a dangerous blow which killed them. However, this is precisely when Luffy’s fruit Awakened and he started using Gear 5. In this form, he was truly equal to Kaido. On some occasions, Luffy could even overwhelm him, however, nobody can say that Luffy’s fight against Kaido was not difficult.