Ovarian collision tumours are rare entities defined by the coexistence of two histologically distinct neoplasms, most commonly reported within the same ovary, while bilateral involvement is extremely uncommon and often under-recognised. Endometriomas are common benign ovarian lesions in women of reproductive age and may be asymptomatic or incidentally detected, whereas mature cystic teratomas are the most frequent ovarian germ cell tumours and are often discovered unintentionally during imaging or surgery. We report the case of a 27-year-old woman in whom adnexal lesions were incidentally identified, with no significant gynaecologic symptoms at presentation. Pelvic magnetic resonance imaging (MRI) showed bilateral ovarian masses, and surgical exploration revealed distinct ovarian lesions involving both ovaries. Histopathological examination confirmed a mature cystic teratoma in one ovary and an endometrioma in the contralateral ovary. This unusual and incidental bilateral presentation highlights the limitations of preoperative imaging in detecting synchronous ovarian pathologies and underscores the importance of thorough intraoperative assessment and definitive histopathological evaluation. Increased awareness of this rare entity is essential to optimise surgical management, fertility preservation and follow-up.