The simultaneous diagnosis of gastrointestinal stromal tumour of the gastro intestinal tract and gastro intestinal adenocarcinoma has been reported many times in the medical literature with various site combinations. We report a case of high risk gastrointestinal stromal tumour of small intestine and polypoid anorectal adenocarcinoma. The uniqueness of this case is that the anorectal adenocarcinoma recurred as a frankly invasive ulceroproliferative growth and the gastrointestinal stromal tumour metastasized to both lungs, liver and bone.