A 50-year-old man having an advanced hepatocellular carcinoma (HCC) was admitted to our institution. An abdominal computed tomogram showed infiltrative mass in the right liver with tumor thrombus invading into the main trunk and contralateral branch of the portal vein. Repetitive transcatheter arterial chemoembolization reduced a tumor size and shrunken portal vein tumor thrombus. The tumor marker levels such as AFP and PIVKA-II decreased. During follow-up, he was diagnosed as having an impending rupture of HCC with acute abdominal pain. He was successfully treated with interventional technique. He died of liver failure 66 months after the first treatment. Although he had a highly advanced HCC with tumor thrombus of the portal vein, repetitive transcatheter arterial chemoembolization therapy may prolong survival.