Yasutora Sado vs. Shunsui Kyōraku

 is Chad's first fight during the Ryoka Invasion. After Sado invades Seireitei along with Ichigo Kurosaki, Orihime Inoue, Uryū Ishida, Ganju Shiba and Yoruichi Shihōin, with the help of Kuukaku Shiba's Cannon, he is separated from the group. Looking for the Shishinrō where Rukia Kuchiki is being held he stumbles upon the 8th Division barracks. As he gets past the guards he is met by Tatsufusa Enjōji, the 3rd Seat of the 8th Division but he is taken care of by a mere blow to the face. then as he proceeds towards his destination he comes face to face with Shunsui Kyōraku the Captain of the 8th Division.

Prologue
Shunsui is among the first Captains to encounter the "Ryoka". He meets up with Yasutora Sado in his division's compound. There, he gently drifts down from a second level to the ground amidst falling petals (scattered by Nanao), then rises to announce his name to Chad.

After his flashy appearance Kyōraku sits down and tells Chad that he dislikes fighting and even offers him something to drink, something Chad responds to by a violent "No" because it is forbidden for minors to drink, something Kyōraku also realizes is a problem.

Battle
Chad proceeds to politely asks the captain to move out the way as he himself would also like to avoid the fight. However, despite Shunsui's humor and his dislike for combat, once Chad engages him, it is seen that he is not a mere fool, but someone not to be taken lightly. He deflects Chad’s first attack with one arm, and then proceeds to dodge all of Chad’s attacks.

Trying to stop Chad from going further, he asks Chad why he continues to fight, and for what reason. Sado tells him that his goal is to save Rukia Kuchiki although he does not know much about her. He says that he was doing it all for Ichigo Kurosaki. Despite his attempts to stop him both through speech and action, Chad continues to come at him.

Seeing his determination, Shunsui decides reluctantly to wound him, though he tells Chad that he plans to kill him, having no choice he takes out his two swords. After reminiscing about the promise that he and Ichigo had made to each other about watching each others back he summons up all of his power and strikes Kyōraku with a massive blow but he misses and finally Shunsui Kyōraku puts an end to the fight, as he swiftly slashes Chad across his chest.

Aftermath
Shunsui acknowledges Sado as an amazingly powerful opponent, for a mere Human. Sado is then seen lying unconscious.

The fight results in Yasutora Sado becoming fatally wounded and Shunsui Kyōraku emerges as the victor. However, he stops Nanao Ise from ending Sado's life and orders her to place him in a holding cell in order to investigate the murder of Sosuke Aizen.