Mature cystic teratomas are benign tumours of the ovary but rarely certain unusual gross and microscopic findings might complicate their diagnosis or may have an impact on their clinical outcome. Here, we are presenting a case series of five unusual pathological presentations of mature cystic teratomas of ovary. Out of five cases, three cases were of collision tumours, in which combination of mature cystic teratoma is seen with mucinous cystadenoma in two cases, and with serous cystadenoma in one case. True collision tumours are defined as histologically distinct neoplasms in the same tissue or organ without any histologic admixture or intermediate cell population zone between two components. These tumours are located in various organs but ovarian location is rare. Mature cystic teratoma is the most common component of collision combinations in the ovary. All classes of ovarian tumours, benign, borderline and malignant may collide and therefore, clinical outcomesin collision tumours depend on individual tumour characteristics. Fourth case was of a mature cystic teratoma associated with a distinct hemangiomatous component. Mature cystic teratoma associated with prominent hemangiomatous component is a very rare finding with only few case reports in the literature and it should be differentiated from true ovarian hemangioma, lymphangioma and angiosarcoma. Fifth case was of bilateral mature cystic teratomas associated with a well-defined lipomatous lesion in right sided mature cystic teratoma mimicking lipoma. Lipomatous ovarian lesions are very rare and mature cystic teratoma with prominent adipocytic proliferation is also an exceedingly uncommon finding and it should be differentiated from true ovarian lipoma and other atypical lipomatous proliferations. Most of these tumours remain clinically and radiologically unrecognized, therefore their histological recognition is essential for adequate patient management.