Patients undergoing pancreatic surgeries have increased by over 50% in the United States over the past two decades. Pancreaticodudoenectomy, or Whipple procedure, represent a major pancreatic surgery involving surgical resection of the pancreatic head to remove cancerous tumors. This study evaluated risk factors associated with increased odds for bleeding and or hemorrhaging complications in patients who underwent pancreaticoduodenectomy. Utilizing a sample of 400 patients who underwent Whipple procedure at the Carolinas Medical Center in Charlotte, NC, a multivariate logistic regression model was generated. The model evaluated several explanatory factors including demographic, co-morbidity, medication, family history, and laboratory variables. The study identified several very significant risk factors including patient’s age, race, cardiac event prior to surgery, use of loop diuretics, steroid use, family history of myocardial infarction, and serum creatinine level, with odds ratios ranging from as low as 2.82 (95% CI: 0.67, 11.97) for a family history of myocardial infarction to as high as 9.15 (95%CI: 1.89, 44.33) for a history of cardiac event. Furthermore, the model identified two factors, systolic blood pressure (adjusted OR: 0.16, 95% CI: 0.03, 0.95) and echocardiogram with stent (adjusted OR: 0.05, 95% CI: 0.003, 0.77) that were protective of bleeding or hemorrhaging complications following the Whipple procedure. In conclusion, this study identified several factors that surgeons can use to identify patients at high risk for post-surgery bleeding complications.