The inferior vena cava (IVC) is the largest single vein in humans. However, during embryogenesis, abnormalities can occur resulting in a duplicated IVC. The portal vein (PV) offers the main blood flood to the liver, forming by the left and right PV. A number of anatomical variations are noticed, underlying the great importance of the pre-operative imaging workup. This case report presents a duplicated IVC and a trifucated PV that were incidentally found in an 82 year-old Caucasian male with pancreatic ductal adenocarcinoma who underwent pancreatoduodenectomy (Whipple procedure). Although some anatomical variations, including the duplication of the IVC and the trifurcation of PV, may be rare to the general population, the suspicion of their existence should always be taken under consideration from surgeons during hepatobiliary or retroperitoneal operations.