Colouterine fistula is an extremely rare condition, as the uterus is a thick, muscular organ. Here, we present two different etiologies for this rare condition-diverticulitis and malignancy. A 77-year-old female with colouterine fistula due to diverticulitis presented with complaints of lower abdominal pain localized particularly in the left iliac fossa and fever. Another case was of 73-year-old female with colouterine fistula due to malignancy who presented with abdominal pain, blood in stools, and whitish discharge from vagina. Both cases were evaluated with contrast-enhanced computed tomography (CECT). The presence of air and fluid within the uterus on ultrasound or CT scan, prompts the possibility of colouterine fistula with CECT providing accurate preoperative assessment.