Background: Head trauma has been proposed as a modifiable risk factor for auditory dysfunction; however, population-based evidence remains limited. This study examined the relationship between head injury severity and multiple audiological outcomes within a healthy ageing cohort. Methods: Cross-sectional analysis was performed using questionnaire and pure-tone audiometry data. Participants were stratified into: no head injury, head injury with loss of consciousness (LOC) without hospitalisation, hospitalisation <24 h, and hospitalisation ≥24 h. Outcomes included self-reported hearing loss, objective pure-tone thresholds, tinnitus, hyperacusis, dizziness, and clinically significant hearing loss (worst-ear >35 dB across frequency bands). Logistic regression generated odds ratios (OR) adjusted for age and sex. Results: Among 5,068 participants, 14.6% reported head injury with LOC. Male sex was strongly associated with head trauma (OR 2.45, p < 0.001). Self-reported hearing loss was significantly more common following head injury (29.8% vs 17.7%; OR 1.98, p < 0.001). Objective high-frequency hearing loss (>35 dB at 4–8 kHz) increased progressively with injury severity, peaking in those hospitalised >24 h (46.3%; OR 1.34 vs controls, p = 0.008). Mean audiometric thresholds were consistently poorer across all frequencies except 250 Hz in those with prolonged hospitalisation. Tinnitus (OR 1.65, p < 0.001), hyperacusis (OR 1.73, p < 0.001), and imbalance (OR 1.50, p < 0.001) were significantly associated with any head injury. Meniere’s disease was more prevalent in severe injury groups (OR 2.9, p = 0.004). Conclusion: Head injury, particularly events requiring hospitalisation are associated with both subjectively reported difficulties and objective deterioration on audiometry. These findings support screening for subclinical hearing loss following traumatic brain injury and reinforce the need for ENT involvement in post-concussive care pathways.