Ruptured hepatocellular carcinoma (HCC) is a well-known serious complication of this most common primary liver malignancy. However, when HCC rupture is associated with other focal liver lesions, the diagnosis and therapy may be very challenging. Correct differentiation of focal liver lesions is of paramount importance for successful treatment. The aim of this report is to present a unique case of HCC rupture complicated with liver abscess, hematoma and portal vein thrombosis. We discuss possible pathophysiological mechanisms and radiologic findings of such clinical scenarios and review literature related to the management of HCC rupture.