Yasutora Sado vs. Shunsui Kyōraku

Yasutora Sado vs Shunsui Kyōraku is Sado's first fight against a formidable Shinigami opponent during the Soul Society Arc. After Sado invades Seireitei along with Ichigo Kurosaki, Orihime Inoue, Uryū Ishida, Ganju Shiba and Yoruichi Shihōin, with the help of Shiba Kuukaku's Canon, he is separated from the group. Looking for the Shrine of Penitence 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.

Battle
Yasutora Sado is surprised at the comic sight that meets his eye with Shunsui Kyōraku making his appearance in a flurry of flower petals apparently being strewn by Nanao Ise his lieutenant. As he tells the captain that he cannot join the skit and asks the latter if he could possibly let Sado pass, Shunsui asks him to stay with him for a drink. Sado tells him that he is a minor and therfore not allowed to drink and charges at him but Shunsui stops the attack from his Brazo Derecha de Gigante with his bare hands and deflects it. Awed, Sado keeps hitting him with all his might but Shunsui dodges all of his attacks. As Shunsui Kyōraku asks him why he is determined to get through even if it meant putting his life on the line, Sado tells him that his goal is to save Rukia Kuchiki although he doesnot know much about her. He says that he was doing it all for Ichigo Kurosaki. After reminiscing about the promise that Sado 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. Shunsui acknowledges Sado as an amazingly powerful opponent, for a mere human. Sado is then seen lying unconscious.

Aftermath
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.