Fluconazole is a bistriazole commonly prescribed for the treatment of various fungal infections caused by yeasts and dermatophytes. However, there have been several reports of rare Adverse Drug Reactions (ADRs) like Fixed Dose Eruption (FDE), Toxic Epidermal Necrolysis and Stevens Johnson Syndrome following oral administration of fluconazole. We report a rare case of fluconazole induced oral mucosal lesions, mimicking herpes labialis, in a 34 year old male patient receiving oral fluconazole for the treatment of allergic fungal sinusitis.