Background: Different techniques of pancreatic anastomosis have been described, with inconclusive results in terms of pancreatic fistula reduction. Studies comparing robotic pancreaticogastrostomy (PG) and pancreaticojejunostomy (PJ) are scarcely reported., Methods: The present study analyzes the outcomes of two case-matched groups of patients who underwent PG ( n = 20) or PJ ( n = 40) after pancreaticoduodenectomy. The primary aim was to compare the rate of post-operative pancreatic fistula., Results: Operative time (375 vs. 315 min, p = 0.34), estimated blood loss (270 vs. 295 mL, p = 0.44), and rate of clinically relevant post-operative pancreatic fistula (12.5% vs. 10%, p = 0.82) were similar between the two groups. PJ was associated with a higher rate of intra-abdominal collections (7.5% vs. 0%, p = 0.002), but lower post-pancreatectomy hemorrhage (2.5% vs. 10%, p = 0.003). PG was associated with a lower rate of post-operative pancreatic fistula (POPF) (33.3% vs. 50%, p = 0.003) in the high-risk group of patients., Conclusions: The outcomes of post-operative pancreatic fistula are comparable between the two reconstruction techniques. PG may have a lower incidence of POPF in patients with high-risk of pancreatic fistula.