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Duodenal adenocarcinoma (DACa) is a rare malignancy, the presenting symptoms of which are vague and nonspecific. We report the case of a patient presenting with symptoms of subacute small bowel obstruction whose CT scan revealed i) left adnexal mass and ii) compression of 3rd portion of duodenum with reduced aortomesentric angle consistent with Wilkie’s syndrome (WS). Laparatomy in addition revealed a distal duodenal stricture, which showed a well differentiated DACa causing subtotal intestinal obstruction. The ovarian mass revealed adenocarcinoma with similar morphology. Immunophenotypic analysis revealed positive expression of CK 20 and CDX 2 and absence of CK 7 staining in the tumours consistent with Primary DACa with ovarian metastasis. We further concluded that the WS resulted from reduced mesenteric fat pad caused by DACa induced cachexia. The case highlights the elusive nature of duodenal malignancy and emphasises the importance of meticulous small bowel examination during exploration of ovarian masses.