Background: Pancreaticopleural fistula (PPF), a form of internal pancreatic fistula, is a rare complication of acute or chronic pancreatitis or pancreatic trauma. Case Report: We report two cases of PPF resulting in formation of pleural pancreatic pseudocysts. A 35-yearold male alcoholic patient with a history of recurrent episodes of acute pancreatitis was admitted due to a severe dyspnea. A CT scan showed a significant left pleural effusion with a total left lung atelectasis, compression of the mediastinum, and dislocation of the left diaphragm. A follow-up CT showed a fistula between the abdominal pancreatic pseudocyst and the left pleural cavity. The second case was a 13-year-old male patient, who was admitted for a splenic stump excision. Two weeks after the surgery the patient presented a massive pleural amylase-rich effusion. CT exam suggested a PPF, which was indirectly confirmed by a thoracoscopy. Conclusions: PPF should be considered in cases of massive pleural effusion and encapsulated pleural fluid collections in patients with a history of acute pancreatitis and surgery involving pancreas.