Purpose Skull base osteomyelitis (SBO) or malignant otitis externa (MOE) is an invasive bacterial infection (a rarely fungal as well as potentially aggressive infection that involves the external auditory canal up to the temporal bone and skull base. This study provides insight into the various clinical presentations of skull base osteomyelitis, the effectiveness of different treatment approaches, and the overall prognosis of SBO based on our case series. Materials and methods This observational study comprises 14 SBO cases, including their diagnosis, follow-up, and treatment. Results Otalgia and purulent otorrhea were observed in all our cases as common symptoms. All patients were diabetic. Three cases (21%) presented with facial palsy and two cases (14%) reported a rare progression of SBO resulting in septic arthritis of the temporomandibular joint. In our study, 43% of the cases diagnosed with SBO had resistance to ciprofloxacin. All our patients had daily cleaning of the auditory canal and the application of antimicrobial ear drops along with long-term systemic antibiotic therapy followed by three weeks of oral antibiotic therapy. All our cases were reviewed after three weeks. Resolution of the disease was achieved. Conclusion Early diagnosis, good control of blood glucose levels, prolonged medical management, and local debridement are likely to result in a better prognosis for patients.