This article describes a case of infectious mononucleosis (IM) in a 16-year-old female adolescent who presented with fever, sore throat, cervical lymphadenopathy and genital ulcerations. Initially, this patient was thought to have herpes simplex viral infection secondary to the characteristic multiple genital ulcers. Seven cases (including this case) have reported an association between Epstein-Barr virus (EBV) infection and genital ulcerations. IM as a cause of genital ulcerations should be included in the differential diagnosis.