Background: Malignant transformation in mature cystic teratoma (MCT) is a rare phenomenon, with squamous cell carcinoma (SCC) being the most frequent histologic subtype. Its diagnosis remains challenging due to nonspecific clinical and radiological findings, and the prognosis is generally poor.

Aim and Objective: To study the early recurrence in case of squamous cell carcinoma arising from teratoma post-surgery and adjuvant chemotherapy: two case reports and literature review.

Case Summary: We present two cases—one ovarian and one extra-gonadal teratoma—with histologically confirmed SCC, both managed with surgery followed by adjuvant Paclitaxel-Carboplatin chemotherapy. Despite this standard management, both cases showed early locoregional recurrence within weeks of treatment completion, highlighting the aggressive course of such malignancies.

Conclusion: These reports underscore the importance of early suspicion, aggressive surgical intervention, and the need for a more tailored adjuvant treatment strategy in SCC arising from teratomas. Further studies are warranted to identify prognostic biomarkers and optimal post-operative management.