Maxillary osteomyelitis is a rare bone infection and is rarer to come across with the advent of advanced antibiotic therapies. It is often linked to immunocompromised conditions, namely diabetes mellitus, cancer, and chronic alcoholism, as they increase the chances of developing osteomyelitis. We present a rare case of maxillary osteomyelitis along with an infraorbital abscess in a 32-year-old male patient with uncontrolled diabetes. The patient complained of dental pain, facial swelling, and visual disturbances. The patient was managed with sequestrectomy along with curettage, incision, and drainage of orbital abscess. The patient responded well to surgery and had no complications post-surgery. As radiographic signs may present late, the authors aim to highlight the significance of thorough clinical examination and good patient history. Prompt radical treatment is necessary to avoid any severe consequences.