This case report describes a 55-year-old man who presented with a swelling below his eye for 5 months. Surgical exploration and biopsy revealed pus and bone erosion. Histopathology showed chronic osteomyelitis due to fungal infection, identified as Aspergillus species. The patient's wound continued draining despite antibiotics. Further imaging and debridement surgery confirmed destruction of the zygomatic arch and maxilla from chronic osteomyelitis. The patient was treated with antifungal medication for 6 weeks.