Development of the vascular system in humans is a complex process that involves formation, retention, regression, and reconnection of primitive vascular channels, ultimately forming a definite pattern of the venous vascular architecture. Any errors in these processes would lead to anomalous venous structures, which would pose severe diagnostic and therapeutic challenges. Herein, we report a case of left-sided inferior vena cava that was noticed in the posterior abdominal wall of a male cadaver aged about 80 years. Although venous anomalies are common in their occurrence, a left-sided transposition of the inferior vena cava is a rare and significant finding in retroperitoneal surgeries because this can be misdiagnosed as para-aortic lymphadenopathy, a tumor or dilated gonadal vein that may result in iatrogenic damage during surgeries. The unusual location and course of the inferior vena cava and its embryological basis are discussed in this case.