Two patients presented with complaints of recurrent drainage of purulent exudate from sinus tracts, inflammation and pain after endodontic re-treatment of the maxillary left (Case 1) and right (Case 2) lateral incisors. The periapical lesions persisted after apical curettage, apicectomy and root-end filling with silver amalgam. Radiographic examination exposed the poor quality of the endodontic treatments and the silver amalgam root-end fillings, which were associated with periapical radiolucent areas in both teeth. The sinus tract persisted after root canal cleaning and shaping, followed by a calcium hydroxide root canal dressing. The root-end fillings were periapically dislodged with endodontic K-files, and showed progressive displacement by sinus tracts up to elimination in the oral cavity. Follow ups of 42 and 65 months post procedure revealed clinical disappearance of the symptoms, sinus tracts and exudates, and radiographs revealed that the repair process of the periapical radiolucent areas was quite advanced.