Malignant transformation (MCT) of ovary is rare complications affecting elderly, squamous cell carcinoma being the most common. The prognosis worsens with extraovarian spread. We present two cases of MCT-derived SCC. Patients exhibited abdominal lump, pain, bowel symptoms, sometimes with weight loss; imaging revealed MCT. Age (51–60), postmenopausal status, large size (>20 cm), bilaterality, and complex ovarian lesions raised suspicion of malignancy. Elevated tumor markers (e.g., cancer antigen-125 and lactate dehydrogenase) were noted in one case. Intraoperative frozen section confirmed malignancy, guiding staging laparotomy. One case was advanced stage on histopathology. Intraoperative frozen section aids optimal staging.