Background: Proximal gastrectomy is a rarely performed procedure but a feasible option in benign tumors and malignant neoplasms in the proximal third of the stomach since novel options of reconstructions are available nowadays with fewer long-term sequels. Methods: Report of three cases of proximal gastric gastrointestinal stromal tumors (GIST), with a description of its presentation, histological characteristics, and follow-up after being treated with proximal gastrectomy with cobra head reconstruction. Results: Case 1: A 62-year-old woman with epigastric pain of four months with endoscopic evidence of a cardia GIST. The surgery was performed without complications. The histopathological report confirmed a fusiform GIST of 3.2 × 3 × 2.5 cm, stage IA. No adjuvant treatment was considered. An esophagogram showed no evidence of reflux and no stenosis, and no disease recurrence after 40-months follow-up. Case 2: A 66-year-old woman with dyspepsia and a palpable tumor in the epigastrium. The surgery was performed without complications. The pathology report confirmed a proximal gastric GIST of 13 × 8 × 7 cm, staged II. She received adjuvant treatment with imatinib for 36 months without recurrence and no reflux or stenosis. Case 3: A 55-year-old woman with intermittent hematemesis and right subscapular pain. The surgery was performed without complications.