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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It's a Japaneese joke. Ukitake's full name is Joshiro Ukitake and Toshiro's full name it Toshiro Hitsuguya. Joshiro and Toshiro sound similar and the names have similar charectors. Also, they both have white hair. Ukitake finds this is perfect reason to give Toshiro gifts, for some reason. It's funny because he always ends up giving it to Yachiru, the vice-captain of squad 11.
Episode # 50 : "Nankurunaisa" .
He dies in episode 32. Diva rapes him and gives him her blood so he crystallises and dies.
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