Background We identified the chronologic changes in the clinical outcomes of minimally invasive distal pancreatectomy (MIDP) for left-sided pancreatic tumors in a single high-volume center over a period of 15 years. Methods Between 2005 and 2019, 2212 patients underwent planned MIDP. Chronologic changes were analyzed according to 5-year intervals (P1, P2, P3). Furthermore, we assessed the prognostic factors of open conversion and postoperative complications. Results Minimally invasive distal pancreatectomy has steadily increased during the last 15 years when compared to open distal pancreatectomy, from 10.8% to 84.9%. Also, MIDP for pancreatic ductal adenocarcinoma (PDAC) has been steadily increasing from 5.6% to 68.4%. According to the 5-year intervals, lengths of hospital stay decreased, but age and American Society of Anesthesiologists (ASA) >= 3 increased; conversely, the rates of Clavien-Dindo classification >= grade 3 (9.5%) and postoperative pancreatic fistula (39.7%) showed no differences. The 90-day mortality and open conversion rates were 0.2% and 3.5%, respectively. Multivariate logistic regression analysis revealed malignancy and extended pancreatectomy were risk factors for open conversion. Furthermore, the poor prognostic factors for severe complications were malignancy, extended pancreatectomy, and ASA >= 3. Conclusion Minimally invasive distal pancreatectomy has become a popular procedure not only for benign cases but also for malignant ones. However, well-organized training, experience and skill are necessary, especially for poor-performance patients and extensively malignant conditions.