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The clinical presentation of gastrointestinal stromal tumours (GISTs) can vary and can be attributed to tumour mass effect or gastrointestinal haemorrhage. We present the rare case of a female in her 50s who presented with an adnexal mass on transvaginal ultrasound, eventually resulting in the resection of a small bowel GIST following diagnostic laparoscopy. A literature review revealed only 26 individual case reports of GISTs initially presenting as gynaecological disease. Mobility of the small bowel and a large-sized tumour promote descension of a mass towards the pelvis. This, along with their non-specific features on imaging, can result in them mimicking gynaecological pathology, prompting initial gynaecological investigation and a delay in surgical management. Non-gynaecological tumours, such as GISTs, must always be considered as a differential diagnosis in patients presenting with pelvic masses or pain.