Background: Intravascular papillary endothelial hyperplasia (IPEH), previously known as ‘Masson’s hemangioma’, is a reactive endothelial proliferation that occurs most commonly in the vessels of the head, neck, and extremities. The cytologic findings of the lesion are varied and depend on the age of the lesion. Cases: Case 1 is a 61-year-old man who presented with a swelling on the medial aspect of the forearm. The clinical diagnosis was lipoma. Cytologic smears showed spindle cells tagging onto a rich capillary network and smaller round cells arranged around hyaline cores. The cytologic diagnosis was benign vascular tumor. On histolopathogic examination a diagnosis of IPEH was given. Case 2 is a 45-year-old man who presented with swelling on the dorsal aspect of the wrist. The cytologic diagnosis of giant cell tumor was made based on the presence of scattered spindled cells and multinucleate giant cells. The giant cells had various shapes like round or crescent and had 10–25 nuclei. The lesion was excised and a diagnosis of IPEH was rendered. Conclusion: These two cases highlight the varied cytomorphology of IPEH making the pinpoint diagnosis of this lesion difficult on cytologic smears.