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He never actually coughs up blood in a current time frame but he is shown coughing up blood in episode 49 (almost the whole episode is a flashback.) Other times he is seen coughing are in episodes 40 which is Ukitake's debut and also in 2 other parts of episode 49 where he just coughs and he doesn't cough up blood.

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15y ago

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Q: In what episode does ukitake cough blood?
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