In performing pancreaticoduodenectomy (PD) or when conducting clinical trials involving PD procedure, a universal platform for predicting the risk of postoperative pancreatic fistula (POPF) is indispensable. In this article, the most significant imaging studies that focused on the objective preoperative assessment of pancreatic pathologies in association with the occurrence of POPF after PD were reviewed. Several recently developed imaging modalities can objectively predict the occurrence of POPF after PD by assessing the elasticity, fibrosis, and fatty infiltration of the pancreas. These valuable imaging modalities include: (1) acoustic radiation force impulse ultrasound (US) electrography which provides information about the elastic properties of the pancreas; (2) contrast-enhanced computed tomography (CT) and magnetic resonance imaging (MRI) with/without contrast-enhancement which reflect the histological degree of pancreatic fibrosis; and (3) multi-detector row CT and/or MRI which reflects the microscopic fatty infiltration of the pancreas. The precise and objective preoperative risk assessment of POPF enables surgeons to customize appropriate management strategies for individual patients undergoing PD. This would be also beneficial for stratifying patients for enrolment in relevant studies that involve pancreatic head resection, as objective criteria could be set for the definitive evaluation of collected data related to surgical outcomes across different institutions and surgeons.