Mature cystic teratomas also known as dermoid cyst are one of the most common benign tumors of the ovary.It is usually seen in young women in the reproductive age group. It comprises of mature elements derived fromall the three germ layers. In this case series we reported a series of 4 cases of mature cystic teratoma of the ovarywith uncommon clinicopathological presentations. First case was a rare entity of melanocytic nevus arising froma mature cystic teratoma. Second case was adipocyte rich teratoma, an uncommon lipomatous lesion of the ovary.Third case was rupture of dermoid cyst presenting as acute abdomen. Fourth case was mature cystic teratoma ina post-menopausal woman. To conclude, though dermoid cysts after surgical removal have an uneventful clinicalcourse, extensive sampling of the specimen for histopathological study should be done to identify rare pathologieswhich bears a clinical significance.