Background: Eagle syndrome is a rare condition caused by elongation of the styloid process or ossification of the stylohyoid ligament, typically presenting with cervicofacial pain, dysphagia, or neurovascular symptoms. Airway compromise has not previously been described as a manifestation. We report an unusual case of Eagle syndrome causing dynamic upper airway obstruction with neck flexion. Case Presentation: A 55-year-old male presented with an eight-year history of persistent right-sided neck pain and a firm submandibular mass, exacerbated by swallowing and yawning. His most concerning symptom was positional dyspnoea occurring during neck flexion, particularly when walking downstairs, requiring frequent neck extension to relieve airway obstruction. Clinical examination revealed restricted neck flexion due to breathlessness and a palpable mass over the right lesser cornu of the hyoid. Flexible nasendoscopy demonstrated posterior collapse of supraglottic structures during neck flexion. Computed tomography of the neck revealed marked bilateral elongation of the styloid process with complete ossification of the stylohyoid ligaments, fixing the hyoid bone to the skull base. Dynamic imaging showed significant airway narrowing at the level of the hyoid during neck flexion. Intervention and Outcome: The patient underwent bilateral division and partial resection of the ossified stylohyoid ligaments via an anterior cervical approach. Immediate postoperative improvement in hyoid mobility was observed, with complete resolution of positional dyspnoea and restoration of neck flexion. Recovery was uncomplicated. Conclusion: This case represents a novel presentation of Eagle syndrome resulting in posture-dependent upper airway obstruction. Complete ossification of the stylohyoid ligaments can cause abnormal hyoid fixation and dynamic supraglottic collapse during neck flexion. Eagle syndrome should be considered in patients presenting with unexplained positional dyspnoea, as timely diagnosis and surgical intervention can be curative.