Purpose This study aims to determine the surgical factors affecting the viability of pancreatic transplants. Methodology A retrospective review of patients who underwent pancreatic transplants SPK surgery at Monash Health between January 1, 2011, and December 31, 2021. Medical records were retrieved, capturing demographic data, transplant characteristics, and post-operative complications. The study evaluated the relationships, as well as the rate and nature of complications associated with these risk factors. Fisher’s exact test was used to determine the association between patient- and surgery-related risk factors and graft failure. Cox regression was performed to determine the hazard ratio of surgical factors towards graft failure. Survival analyses using the Kaplan-Meier test were applied to functioning and failed grafts. Results A total of 130 patients with 132 pancreatic transplants were included in this study. Post-transplant complications included rejection (25.0%), vascular thrombosis (13.6%), haemorrhage (15.9%), and pancreatitis (6.1%). Pancreatic graft failure occurred in 22.0% of transplants, while mortality was 10.8%. Portal vein extension was associated with increased graft failure (p=0.034) with a hazard ratio (HR) of 3.20 (CI: 1.14-8.97, p=0.027). Anastomosis to the external iliac vein also showed a high risk of graft failure with HR: 3.02 (CI: 1.31-6.97, p=0.010). Recipient inferior vena cava anastomosis was protective with HR 0.26 (95% CI 0.12–0.56, p=0.001). Patients with graft failure are at higher risk of mortality with HR 3.87 (CI: 1.36-11.04, p=0.011) than those with functioning grafts. Conclusion Portal vein extension and recipient external iliac vein anastomosis are the primary risk factors of pancreatic graft failure. Anastomosis to the IVC is recommended in pancreatic transplants.