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Squamous cell carcinoma (SCC) of the ovary is a rare malignancy, most commonly arising from malignant transformation within a mature cystic teratoma (MCT). The incidence of such transformation is estimated at around 2%. We report the case of a postmenopausal woman who initially underwent resection of a pelvic mass with right adnexectomy. Histopathological examination revealed squamous cell carcinoma arising in a mature ovarian teratoma. The case was subsequently discussed at a multidisciplinary tumor board, which recommended completion surgery. However, during the planned procedure, diffuse peritoneal carcinomatosis was discovered intraoperatively. The patient was therefore referred for neoadjuvant chemotherapy. This case highlights the diagnostic and therapeutic challenges of SCC arising in MCT, as well as its aggressive clinical course.