Shunsui Kyōraku & Jūshirō Ukitake vs. Genryūsai Shigekuni Yamamoto

 is a fight between the pair consisting of Captains Jūshirō Ukitake and Shunsui Kyōraku and Captain-Commander Genryūsai Shigekuni Yamamoto.

Prelude
Earlier Ichigo Kurosaki had arrived to stop the execution of Rukia Kuchiki at Sōkyoku Hill. As the Sōkyoku moved to make a second attack, Captain Ukitake intervened by using the Shihōin Shield. Together with Kyōraku, the two destroy the Sōkyoku. Surprised at the actions of Ukitake and Kyōraku, Captain Suì-Fēng moved to end Kiyone Kotetsu and Sentarō Kotsubaki for being part of Ukitake's "treachery." Ukitake yells for Suì-Fēng to wait, but Captain-Commander Yamamoto quickly intercepts him. Yamamoto orders them to not move as the person who made off with Rukia was a replaceable lieutenant. He then states that he cannot forgive them, noting on the severity of the two captains' crimes. Kyōraku then grabs Ukitake and makes a hasty retreat off the cliff. Though Ukitake protests with concern over his 3rd Seat Officers, Kyōraku tells him to calm down as they would be fine and fighting Yamamoto there would drag the others into their fight. As such the two decide to run through Seireitei to create enough distance so that no one else would get involved. Arriving in ruins somewhere in Seireitei, the two choose to stop, having created enough distance away from all other combatants. Lieutenant Nanao Ise, who had followed the pair, is teased by her captain for arriving last. She then notices that Yamamoto had already beaten them there. Kyōraku notes that he is amazed that Yamamoto had out-sped them to which Yamamoto comments on how his targets do not escape him and that they wouldn't "get off without a thrashing."

Battle
The battle begins with Yamamoto walking towards the trio. As he proceeds, Nanao notes on Yamamoto's legendary and terrifying Reiatsu. Seeing as they would have a very slim chance of winning even with two captains, Nanao moves to draw something from her robes to help. She then is completely paralyzed by Yamamoto's Reiatsu just by making eye contact with him. As she begins to collapse, Kyōraku immediately places himself between the two. He consoles Nanao as he picks her up, using Shunpo to get her to a safe distance from the fight, before returning to Ukitake's side. After praising Kyōraku for his display of Shunpo, Yamamoto expresses his disappointment over his most promising and strongest disciples' decision to turn against him. He holds his wooden staff sideways, and its wood unravels, revealing his sheathed Zanpakutō. As he draws his sword, he urges for Ukitake and Kyōraku to do the same, telling them that it is too late for words. The two instead place their hands on their hilts.

Yamamoto slashes through the air, causing the two to jump back from the force of Reiatsu in Yamamoto's swing. Yamamoto scolds them for not releasing their Zanpakutō. Kyōraku attempts to reason with him to not fight, saying that sometimes they must carry out justice on their own terms. Ukitake backs Kyōraku, reasoning that it was Yamamoto who had taught them that. Yamamoto calls this foolish as they must carry out the true justice of the world. Ukitake then speaks up, asking what is the true justice of the world and who determines what is right and wrong. Yamamoto reminds them again that the time for speaking has passed. He takes off his outer garbs to reveal a well toned and battle-scared physique underneath. He then releases his Zanpakutō, Ryūjin Jakka.

While Ukitake and Kyōraku look on at their old teacher, the area around the three combatants is surrounded by walls of flame. Ukitake thinks to himself about Ryūjin Jakka's incredible and frightening power. For the last time, Yamamoto urges his two disciples to release their Zanpakutō. Realizing they have no other option, they oblige with Ukitake releasing his Sōgyo no Kotowari first. Kyōraku follows up by releasing Katen Kyōkotsu. Yamamoto praises them for having the only two dual Zanpakutō in Soul Society, noting how they have not changed at all. He asks if the two are prepared, to which the two confirm before they rush towards each other. The result is a very large explosion from the clash between the three powerful Shinigami.

Aftermath
Most of the battle is not shown. However, the three of them are last seen as Lieutenant Isane Kotetsu uses Tenteikūra to disclose information to them about Sōsuke Aizen's betrayal to Soul Society. Realizing how pointless their fight was, they ended their battle and headed off to Sōkyoku Hill. All three are battle-worn, but relatively uninjured. Ukitake and Kyōraku, however, are shown to have some bleeding on their heads.