Donovanosis is a rare, chronic and indolent sexually transmitted infection caused by Klebsiella granulomatis. The ulcers in donovanosis rarely undergo malignant transformation, which is usually seen in longstanding ulcers. We present a case of a 32-year-old male who presented with a two-month history of rapidly progressive, large, foul-smelling ulcers over the groin, distal penile shaft and scrotum. Crushed tissue smears from ulcers revealed basophilic intracellular and extracellular Donovan bodies. Fine needle aspiration cytology from inguinal lymph nodes and biopsy from the ulcers revealed well-differentiated squamous cell carcinoma. The current case aims to alert clinicians that donovanosis is a rare but possible cause of cutaneous malignancy. Nonetheless, the pathogenesis of malignant transformation in donovanosis needs further research.