Objective: This study aimed to determine the cytodiagnostic spectrum of various male breast lesions, which were corroborated on histopathology asappropriate, to describe the process of the cytomorphology of some uncommon pathological lesions, and to discuss the reasons of their misdiagnoses.Materials and Methods: In this 8-year study, a total of 114 patients underwent fine needle aspiration cytology (FNAC). In a representative case, nippledischarge from an 8-month-old child was examined. Confirmatory histopathology was obtained in 38 cases only.Results: Gynecomastia was the most common (63.5%) male breast pathology. Invasive breast carcinoma of no special type was the most common variantof male breast malignancy. Half of the “gray zone” of cytological lesions was confirmed as cancer, but the rest were diagnosed as fibrocystic disease andintraductal papilloma. All cases with malignant cytology matched their corresponding histopathology. However, a tumor from an intraductal papillarycarcinoma was miscued as ductal carcinoma on previous FNAC.Conclusion: Cytological evaluation of male breast lesions provides highly sensitive and specific results with excellent histologic reproducibility. Thus, itshould be the ideal pretherapeutic diagnostic procedure for male breasts. However, some benign pathological conditions, which are particularly associatedwith epithelial hyperplasia, perplex the cytomorphologic scenario into the “gray zone.”