Inflammatory bowel diseases (IBD), including ulcerative colitis, are chronic autoimmune conditions characterized by inflammation of the digestive system. The exact cause of IBD is unknown, but they often start during adolescence or early adulthood with symptoms such as urgency, rectal bleeding, diarrhea, abdominal pain and tenesmus. Primary sclerosing cholangitis and autoimmune hepatitis are recognized as co-occurring conditions associated with ulcerative colitis. However, the combination of ulcerative colitis, primary sclerosing cholangitis, liver cirrhosis, and celiac disease occurring concurrently has only been reported once before in a female patient. Here, we present the exceptional case of a Syrian adult male with all four of these conditions. This highlights the importance of screening for both celiac disease and cirrhosis in patients with ulcerative colitis and primary sclerosing cholangitis together, despite this combination of comorbidities is rare.