Endometriosis is well known as a chronic condition associated with significant morbidity. Umbilical endometriosis, however, may go unrecognized because of its rarity, leading to multiple medical visits and a delayed diagnosis. Chronic umbilical drainage is an unusual presentation for umbilical endometriosis. Even more unusual is the development at this location in a patient without previous abdominal surgery. There are very few published case reports about primary umbilical endometriosis. A 24-year-old nulliparous African American woman presents to the emergency department with a complaint of chronic umbilical drainage of 3-year duration and undergoes a computed tomographic scan and subspecialty referral, which lead to the diagnosis of primary abdominal wall endometriosis and a new left ovary endometrioma. Although this is an unusual occurrence, it may be considered in patients with chronic umbilical drainage without other cause.