Persistent tracheopharyngeal (TPF) and tracheo-oesophageal (TEF) fistulas after laryngectomy create a therapeutic challenge. The current classification of TPFs and TEFs is based on clinical experience without detailed anatomical information. In this study, casts of TPFs/TEFs were obtained from 16 patients; these were the first steps in manufacturing customised prostheses. Fistulas were classified according to the shape and dimension of the tracheopharyngeal and tracheo-oesophageal silicone casts and prostheses as well as on epithetic requirements. Four different types of fistulas were classified: Type A, a fistula with a straight axis between the neopharynx and oesophagus; Type B, a fistula with a stenosis of the neopharynx but a straight axis; Type C, the axis between the neopharynx and oesophagus is flexed anteriorly; and Type D, neighbouring structures are absent creating a large defect. This classification system might improve the manufacturing processes of customised prostheses in individual cases with challenging tracheopharyngeal and tracheo-oesophageal fistulas.