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We report a diagnostically challenging case of polymicrobial orbital apex syndrome in an immunocompromised patient, emphasizing the importance of early multidisciplinary intervention and consideration of fungal aetiologies in high-risk individuals. A 70-year-old woman with multiple comorbidities presented with subacute left orbital pain and frontotemporal headache, with early signs of cranial nerve VI palsy. Despite initial stability, the patient deteriorated over 2 weeks, developing complete left ophthalmoplegia, proptosis, and vision loss. Further investigation demonstrated a polymicrobial skull base osteomyelitis with orbital apex and cavernous sinus involvement. Histopathology revealed necrotic material with chronic inflammation, and cultures identified Aspergillus flavus, Pseudomonas aeruginosa, Staphylococcus aureus, and Candida parapsilosis. The patient was treated with intravenous vancomycin, oral ciprofloxacin, and voriconazole for 6-8 weeks. Diagnosing orbital apex syndrome in immunocompromised individuals is complex and early imaging is critical. A high clinical suspicion for fungal infection should be maintained, with a strong role for timely tissue diagnosis. Coordinated multidisciplinary care and targeted antimicrobial therapy can prevent further morbidity from intracranial extension.