Introduction Complications associated with the administration of local anaesthesia are rare, with the majority being local or self-limiting. Case report A single case where severe unilateral headache associated with left sided inferior alveolar nerve block injection is reported. A history of a traumatic brain injury on the ipsilateral side was a potential factor. The strategy used to produce local anaesthesia without a recurrence of the headache is described. Conclusion A logical approach to the history taking and treatment planning resulted in a successful outcome for the patient, using commonly practised local anaesthetic techniques.