Gastro-intestinal Stromal Tumours (GIST) are common mesenchymal tumours of the gastrointestinal tract. We report a case of a patient presenting with massive hematemesis, malena, hypotension and severe anemia. There was 7x7cm ulcerated bleeding gastric polyp on posterior gastric wall on endoscopy. Laparoscopic excision of polyp was performed successfully with anterior gastrotomy approach. Histopathology revealed a benign spindle cell tumour (GIST) with clear margins. This case is being presented due to the peculiar mode of presentation with massive UGI bleed (rare mode of presentation of GIST) and peculiar morphology of the GIST which presented as a polyp rather than a submucosal mass. This case report highlights the necessity of early surgical intervention in such cases to avoid mortality due to bleeding and to raise the awareness of rare causes of upper gastrointestinal bleed and their management.