We report a rare case of a patient who underwent 3 successful curative operations for the metachronous appearance of pancreatic cancer. In July 2007, a 54-year-old woman underwent pylorus-preserving pancreaticoduodenectomy. In March 2010, a tumor measuring 9 mm in diameter was detected in the tail of the pancreas on computed tomography (CT) and magnetic resonance imaging. The pancreas tail was subsequently resected while preserving the pancreatic body. In February 2011, CT revealed a cystic tumor measuring 2.5 cm in diameter in the remnant pancreatic body without any metastasis; therefore, total resection of the residual pancreas was performed in April 2011. The first resected tumor was histopathologically diagnosed as undifferentiated adenocarcinoma with osteoclast-like giant cells. Additionally, the third resected tumor had similar undifferentiated components. Contrarily, the second resected tumor was diagnosed as a well-differentiated tubular adenocarcinoma. We consider that the tumor from the third operation was an intra-pancreatic metastasis of the primary cancer and that the tumor from the second operation was the second primary cancer. The patient responded well with good control of surgical diabetes for 92 months since the last pancreatectomy. This case suggested that aggressive repeated resection for recurrent pancreatic invasive ductal adenocarcinoma is beneficial in limited cases.