Kaido fought Luffy and Zoro from chapter 923 to chapter 1049. Chapter 923 (episode 915): Luffy lost to Kaido. Chapter 1010: Zoro lost to Kaido; no contest for Luffy. Chapter 1013 (episode 1033): Luffy lost to Kaido. Chapter 1042 (episode 1069): Luffy lost to Kaido. Chapter 1049 (episode 1076): Luffy beat Kaido.
Enraged by the attack on his crew, Luffy assaults Kaido with Elephant Gatling and Gear Fourth Boundman in Kuri; Kaido stands up sober and blitzes Luffy with a single Raimei Hakke, knocking him out cold.
FILING NOTE
Kaido incapacitates Luffy in a single strike at CH. 923 · EP. 915.
On the Onigashima rooftop, the five Supernovas clash with Kaido and Big Mom; Law removes Zoro from danger and Zoro scars Kaido with Asura, but Kaido's Raimei Hakke strikes the two of them down, and Luffy coats his fists in Conqueror's Haki to knock Kaido down as the group disperses.
FILING NOTE
Files NC because the rooftop group breaks apart while Luffy continues facing Kaido without a decisive result at this point.
Reaching his absolute limit atop Onigashima, Zoro unleashes Kyutoryu: Asura Bakkei Dead Man's Game and carves a permanent scar across the Emperor's chest before collapsing, and Kaido's Raimei Hakke then strikes him down beside Law.
FILING NOTE
Files L because Zoro is worn down by the fight and struck down by Kaido's own Raimei Hakke while the Emperor stands, and it files at CH. 1010, where that happens.
Duelling Kaido one-on-one atop Onigashima, Luffy's unrefined Conqueror's Haki infusing is overwhelmed; Kaido batters Luffy unconscious and watches him plunge off the floating island into the sea.
FILING NOTE
Kaido defeats Luffy and knocks him off Onigashima at CH. 1013 · EP. 1033.
In the climax of their Onigashima rooftop duel, CP0 agent Guernica intervenes to restrain Luffy; Kaido's Roaring Thunder Bagua strikes Luffy point-blank, crushing his skull and stopping his heart before his awakening.
FILING NOTE
Kaido strikes down Luffy at CH. 1042 · EP. 1069 following outside CP0 interference, filing a loss for Luffy and a partner win for Kaido.
Awakening Gear Five as the Sun God Nika, Luffy manifests an island-sized fist infused with Conqueror's Haki and overpowers Kaido's Flame Dragon Torch with Bajrang Gun, drilling the Emperor deep into Wano's magma chamber.