Secondary sclerosing cholangitis in critically ill patients (SC-CIP) is a rare cholestatic liver disease triggered by long-term intensive care treatment. The aim of this study was to evaluate the frequency and characteristics of gastrointestinal bleeding in SC-CIP. Patients with diagnosed SC-CIP were retrospectively identified and compared to a control group of patients with cardiac surgery and intensive care treatment but without the development of SC-CIP. Fifty-three patients with SC-CIP and 19 controls were included in the study. The frequency of gastrointestinal bleeding was 30% in SC-CIP (16 patients) and 5% in the control group (1 patient) (p = 0.03). Bleeding occured in the mean 13 months after admission to an intensive care unit in SC-CIP, three patients (19%) suffered bleeding during intensive care treatment. Three SC-CIP patients (19%) had cirrhosis at the time of bleeding, five (31%) had splenomegaly, and four (25%) received oral anticoagulation. In SC-CIP, 13 bleedings were identified in the upper gastrointestinal tract, two in the lower, and one remained unknown. The most common reasons for bleeding were gastroduodenal ulcers. In total, 80% of patients needed blood units, and one death due to bleeding occurred in SC-CIP. In conclusion, gastrointestinal bleeding is a frequent complication in patients with SC-CIP. Whether the liver disease itself or cofactors cause the susceptibility for bleeding remains unclear.