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Transverse vaginal septum (TrVS) is a rare congenital anomaly of the Müllerian duct system that leads to obstructed menstrual flow. We present a case of a teenage girl with primary amenorrhoea, cyclic pelvic pain and a high transverse vaginal septum associated with haematocolpos and a septate uterus. Initial resection under laparoscopic guidance provided temporary relief, but postoperative complications such as vaginal stricture and adhesions developed due to non-compliance with dilation therapy. Secondary surgery involved stricture release and placement of a collagen-elastin scaffold (Matriderm) to prevent re-adhesion. At the 6 week follow-up, vaginal patency was maintained with restored menstruation. This case emphasises the need for structured follow-up and emerging reconstructive strategies for optimal outcomes.