Nipple discharge (ND) either in the presence or in the absence of underlying mass is a very uncommon presentation in males and its bloody nature is still rarer. ND cytology in males has not been reported much in the literature. Spontaneous and expressed ND, however, can be very useful in establishing the diagnosis. Two males with bloody ND, one, without any palpable mass and another with underlying mass, were evaluated on ND cytology. The presence of loose papillaroid clusters and cell sheets with mild atypia was seen in ND smears itself in case 1. The discharge was more copious in case 2, but the ND smears were paucicellular. The presence of tall columnar cells in ND smears as well as in the FNA from underlying mass with clear features of malignancy was helpful in reaching the diagnosis of papillary carcinoma in case 2. Histopathology in case 1 was a spectrum of ADH to DCIS, whereas in case 2, was tubulopapillary carcinoma. Following two cases highlight the importance of the cytological evaluation of ND smears.