Purpose: Pancreaticoduodenectomy (PD) is a complex and invasive procedure. Post-pancreatectomy haemorrhage (PPH) can be catastrophic, with a 20% mortality rate. Patient’s PPH risk stratification is critical to ensure early recognition and management. Methodology: A retrospective cohort study was conducted on all PD patients from January 2022 to December 2023. Patient demographics and clinicopathological outcomes were analysed using SPSS v.29. Results: Eighty-two patients underwent PD, with most having a classic PD (n=65, 79.3). Males comprised (62.2%), with a median age of 68 (IQR14) and a median BMI of 25.3 (IQR6.8). Median surgical time and LoHS were 449.5 minutes and 11 days, respectively. The overall PPH rate was 12.2% (95% CI [6.0-19.3]), and the mean time to PPH was 12.1 days (SD±8.5). Univariate analysis showed a significant correlation between PPH and abnormal day 3 (D3) drain amylase (p=.02), a non-decompressed biliary system (p=.03), soft pancreatic consistency (p=.04), ileus (p=.04), and post-operative pancreatic fistula (p=.01). Multivariate logistic regression controlled for potential and non-significant confounders and showed that an abnormal D3 drain amylase was significantly and independently associated with PPH (OR 6.9, p=.03). Furthermore, ROC analysis determined that a D3 amylase above 241 U/L was significantly predictive of PPH (p<.01, model quality of 0.78) with a sensitivity of 100% and specificity of 75%. Conclusion: This study demonstrated the utility of D3 drain amylase in predicting PPH. The D3 drain amylase ROC cut-off value of 241 can be a valuable addition to the surgeon armamentarium to aid with risk stratification, early identification and optimal management.