God-Eneru" -"Luffy vs. Donquixote Doflamingo". Therefore, "Luffy vs. Commander Dogtooths" is currently Luffy's longest fight (in terms of pages).
The longest fight in #anime history goes to One Piece. The Luffy vs. Katakuri fight lasts for 21 episodes.
With the War For Wano apparently coming to an end, the battle against Kaido hasn't just been one of the largest scale battles of the series to date, but it has also been the longest, as One Piece fans have noted just how lengthy the battle against the Beast Pirates has been.
The fight lasted 9–12 hours, depending if you count their breaks into it. Katakuri did a break to eat donuts, Luffy to recharge his Haki. When Luffy was keeping up to Kata, the fight lasted 2–3 hours including I think 30 minutes in Gear 4.
Smoker. Luffy's first proper defeat in One Piece came at the hands of Smoker, who served as a Marine Captain back during the Logue Town arc. Being a Logia type made of smoke, it was impossible for Luffy to beat Smoker. The battle between the two wrapped up quite quickly and ended in favor of Smoker.
Yeah, he's lost more than once. Crocodile did beat him twice before his defeat, Aokiji and Kizaru handed his ass to him and Kaido one shotted him.
However, that's not to say that Kaido has never lost. It is a known fact that Kaido has lost to his fellow Yonko and the Navy a combined 7 times and been captured a total of 18 times.
With his strongest attack, called Bajrang gun, Luffy sent Kaido crashing from Onigashima into the underground of Wano. Kaido was completely knocked out by the ferocity of Luffy's strike and ended up in the same place as Yonko Big Mom.
Monkey D. Luffy defeated Kaido. Luffy and Kaido fought on two different occasions. Luffy first fought with Kaido when Kaido had destroyed Oden's castle.
Straw Hat Pirates vs. 100,000 Opponents" is the 554th episode of the One Piece anime.
Second while luffy was poisoned by the jailor at impel down and ivankov treated him, ivankov told luffy the treatment would consume 10 yrs of his lifespan.
5/10 He Was Almost Killed By Crocodile
Crocodile left Luffy with a critical injury and tossed him into quicksand to ensure his demise. At the time, this was the worst defeat Luffy had suffered and if it was not for Nico Robin, he never would've escaped the quicksand.
One Piece 1049 marked a spectacular conclusion to the fight between Luffy and Kaido as the fist carrying the weight of 20 years finally landed and struck the Yonko into oblivion.
On April 6, 1893, Bowen and Jack Burke fought the longest fight in history. Bowen had originally scheduled the fight with another opponent, however after dropping out of the fight, Jack Burke, who was the latter's trainer, fought the bout instead.
Chapter 1040 saw the momentous defeat of one of these emperors, Charlotte Linlin, better known by her epithet "Big Mom". Big Mom's defeat by Luffy's allies (for the time being) Trafalgar Law and Eustass Kid, has major implications for the future of One Piece.
Garp is a Vice-Admiral of the Marines. Being their strongest known member in history, there's no denying that Garp is capable of taking on Kaido. He's previously fought against the likes of Rocks, and even Gol D. Roger.
Whether Shanks can defeat Kaido or not is unknown, but he is certainly on par with Kaido, if not stronger. Interestingly, the two have already fought once in the New World, and Shanks emerged unscathed at Marineford after the fight.
He is known as the "Strongest Creature Alive" and possesses a mythical zoan devil fruit that allows him to turn into an Eastern Dragon. Demonstrating his might, Kaido took out Luffy with one swift strike. Almost all the Yonko are equal in strength and it wouldn't be at all surprising if Kaido could defeat Shanks.
Probably no, Mihawk can't cut even Diamond Jozu with his one of the strongest slash and King Elizabello's punch can't broke Bartolomeo's barrier. Mihawk can't win against Kaido who had insane strength that is enough to destroy half of an island.
Crocodile is easily one of the most difficult fights that Luffy has ever fought as he lost to him twice. In fact, Luffy would've died both the times had luck not been on his side.
Having betrayed Whitebeard and hunted the Straw Hats since Mock Town, Blackbeard is Luffy's greatest remaining threat. Considering the Devil Fruit and powerful crew under his command, the villain won't go down easily regardless of the things Luffy learned and friends he's made.