Tumours of the small intestine are among the rarer conditions as compared to other tumours of the gastrointestinal tract. Among these, sarcomas hold a much lesser number in proportion to adenocarcinomas. Leiomyosarcomas occurring in the small intestine constitute an even smaller number, accounting for about 1% of malignant mesenchymal lesions in the gastrointestinal tract. Within the spectrum of LMS of the small intestine, the more common location encountered is the ileum, followed by the duodenum. The second part of the duodenum is usually implicated in most studied and reported cases of duodenal LMS. These tumours are known for their aggressive nature and their often-delayed presentation due to ill- defined symptomatology and diagnostic challenges. As a result of the above, even a century after the first reported case, their prognosis is poor. Here we report a case of a 64-year-old female who presented with vague complaints of abdominal discomfort and dyspepsia for a month and was diagnosed to have a mass lesion in the 2nd and 3rd part of the duodenum. Intraoperatively, she was found to have two separate mass lesions in D1 and D3 and was subjected to a pancreaticoduodenectomy. The mass lesions were pathologically categorized as leiomyosarcomas of the first and third part of the duodenum.