Infantile osteomyelitis is a rare disease that is infective in nature and may rapidly turn fatal, as the disease is often misdiagnosed due to its varied presenting signs. Early diagnosis may help in avoiding systemic involvement and permanent deformity. The disease presents with signs of orbital involvement, nasal congestion, and emesis, as well as other standard hallmarks of infection. Furthermore, the maxilla is a highly vascular and porous bone and the occurrence of osteomyelitis in an infant maxilla is highly uncommon. In addition, routine blood work is not suggestive of the presence of this disease. Thus, prompt diagnosis of this condition poses a challenge to surgeons due to the confusing array of symptoms combined with the rarity of the disease. One such case of osteomyelitis of the maxilla in a young child is presented. The dilemma encountered by the surgeon during the diagnosis and treatment of the disease is discussed.