Introduction Bezold’s abscess is a rare potentially life-threatening deep neck abscess complication of otomastoiditis. Primary tuberculous otomastoiditis is a rare temporal bone complication which comprises only 0.04-0.9% of all chronic otitis media cases. A concomitant tuberculous otomastoiditis and bezold’s abscess is very rare with currently few reports up to this day. Objective To present a rare case of Bezold’s Abscess with Drug Resistant Tuberculous otomastoiditis in a 20-year-old Male and its dilemma on prompt recognition and management. Results A 20-year-old male presented with a three-month history of right otorrhea. This was not associated with otalgia, tinnitus, hearing loss, facial asymmetry, fever, and chills. He was initially treated with antibiotic which afforded minimal symptom relief. Physical examination revealed a perforated tympanic membrane with purulent discharge and right fluctuant lateral neck mass. Temporal bone and neck CT scan revealed soft tissue mass occupying the right external auditory canal, abscess formation at the right perivertebral and posterior cervical space, thinned out tegmen tympani and eroded middle ear structures. The patient underwent canal wall down mastoidectomy and incision and drainage of neck abscess. Lateral Neck Abscess and Temporal Bone Tissue studies revealed Mycobacterium tuberculosis which was Rifampicin-resistant and Pseudomonas aeruginosa. The postoperative period was unremarkable. The patient was started on Levofloxacin-Bedaquiline-Linezolid-Clofazamine. He was registered under the SLORD FQ-S (Standard Long Oral Regimen for Fluoroquinolone Susceptible). On follow-up, patient had good secondary intention healing with the resolution of otorrhea. Discussion Our index case presented with tuberculous otomastoiditis complicated with Bezold’s abscess and with Pseudomonas aeruginosa isolate. It posted a dilemma in diagnosis as the patient’s clinical presentation mimics that of common pathologies such as a cervical reactive lymphadenitis. This eventually also contributed to the dilemma of management due to the delay of proper initiation of surgical intervention. Transpired events led to a middle ear erosion to form a cervical abscess progressing to a Bezold’s abscess. Case reports mentioned a mastoidectomy should be done urgently especially if complications are present. This is in addition to cervical drainage of the abscess. The patient underwent an mastoidectomy, incision and drainage of lateral neck abscess. The presence of Mycobacterium Tuberculosis in the specimen is a rare occurrence, ever more so that it was resistant to the usual six-month medical therapy which includes Isoniazid, Rifampicin, Pyrazinamide, Ethambutol (HRZE). The patient was deemed eligible to be enrolled in the SLOR FQ-S (Standard Long All Oral Regimen for Fluoroquinolone Susceptible Strains) program of the country. This entails a six-month regimen of Levofloxacin-Bedaquiline- Linezolid-Clofazamine, followed by 12-14 months of Levofloxacin- Linezolid-Clofazamine. Bezold’s abscess is a complication which resulted in abscess pocket formation, thinned out tegmen tympani, and eroded middle ear structures which mandates continued postoperative care and close monitoring. This degree of an event is due to the paucity of occurrence. The lack of published local data and international data at present resulted in a low index of suspicion in clinicians. No standardized guidelines have been published addressing the timely diagnosis and management. This case also highlighted the importance of proper coordination with the National Tuberculosis Control Program by the Department of Health for patient registry and monitoring of treatment status of confirmed patients. Recommendations Tuberculous otitis media with concomitant Bezold’s abscess is a possible sequela of untreated otitis media. For countries where tuberculosis is still endemic, a high level of suspicion for tuberculous otomastoiditis is warranted for cases of complicated otitis media.