Gynecological pelvic masses are a common occurrence in women of all ages. The differential diagnosis is extensive and includes masses of all anatomical components of the female reproductive tract. This simple and refined approach leads the reader through the process of narrowing said differential. A thorough history and physical examination are essential steps that can hint to the appropriate investigations such as reproductive hormone levels, serum cancer biomarkers and imaging. Emphasis is put on ultrasound findings, helping differentiate not only diagnoses, but also the benign or malignant character of the mass. It also highlights the Risk of Malignancy Index I, commonly used in clinical practice to assess the risk of malignancy of a mass. Beyond the initial approach, some diagnoses and their management are discussed, from the very common functional cyst to the worrisome ovarian neoplasm, and mentioning more peculiar findings like tubo-ovarian abscess and leiomyoma.