A 64-year-old man originally underwent Bentall procedure for annulo-aortic ectasia for the first time at the age of 38 years. The surgery was to repair a pseudoaneurysm at the anastomotic site of the left coronary artery by direct closure 11 years after the first Bentall procedure. The anastomosis of the right coronary artery was normal at the time of the first reoperation. However, he had surgery to repair a pseudoaneurysm at the anastomotic site of the right coronary artery 26 years after the first operation ; this was accomplished using the button technique. However, seven months after the second reoperation, he again manifested a pseudoaneurysm at the anastomotic site of the left coronary artery and died of rupture of the pseudoaneurysm. We report the case of pseudoaneurysms at the right and left coronary artery anastomoses that occurred three times after the first Bentall procedure.