Endometriosis is a common gynaecological condition affecting about 6–10% of women of reproductive age and can be a debilitating disease. It is the second most common reason for surgery in premenopausal patients. It is defined as the presence of endometrial-like tissue outside the uterine cavity, leading to a chronic inflammatory reaction. The exact aetiology is unknown, but the retrograde menstruation model is the most widely accepted theory explaining the development of pelvic endometriosis. According to this model, menstrual blood containing endometrial fragments passes through the fallopian tubes into the pelvic cavity, resulting in the formation of peritoneal endometrial deposits. There are three distinctive pathological types of pelvic endometriosis: superficial peritoneal implants, ovarian endometriomas, and deep infiltrating nodular lesions. The extent of the disease is very variable and often does not correlate with the severity of symptoms. Although it can sometimes be asymptomatic (in about 20% of cases), endometriosis is frequently associated with severe pain and infertility. Several management options exist for endometriosis and the choice depends on several factors such as age, fertility, severity of the symptoms, and extent of the disease. This review presents three different cases of endometriosis with different complexities and presentations. The diagnosis and various medical and surgical treatment options available to the clinician will be discussed.