Objective. Imperforate hymen represents the extreme in the spectrum of hymenal embryological variations. The archetypal presentation in the adolescent patient is that of cyclical abdominopelvic pain in the presence of amenorrhoea. We reported a rare event of imperforate hymen presenting as a cause of tuboovarian abscess (TOA). Case Study. A 14-year-old girl presented to the emergency department complaining of severe left iliac fossa pain. It was her first episode of heavy bleeding per vagina, and she had a history of cyclical pelvic pain. She was clinically unwell, and an external genital examination demonstrated a partially perforated hymen. A transabdominal ultrasound showed grossly dilated serpiginous fallopian tubes. The upper part of the vagina was filled with homogeneous echogenic substance. Magnetic resonance imaging (MRI) demonstrated complex right adnexa mass with bilateral pyo-haemato-salpinges, haematometra, and haematocolpos. In theatre, the imperforate hymen was opened via cruciate incision and blood was drained from the vagina. At laparoscopy, dense purulent material was evacuated prior to an incision and drainage of the persistent right TOA. Conclusion. Ideally identification of imperforate hymen should occur during neonatal examination to prevent symptomatic presentation. Our case highlights the risks of late recognition resulting in the development of sepsis and TOA.