Background/Objective. Headaches present commonly in general practice, and doctors face uncertainties and pressures in dealing with them. This study identifies key characteristics of headaches investigated through head imaging, in the hope of strengthening existing guidelines. Method. A 7-year retrospective analysis of head imaging scans ordered for investigating headaches among patients aged ≥18 in an Australian general practice setting. Results. A total of 109 of the 517 (21.1%) patients required head imaging, although 14 (2.7%) of these had repeat scans. Three-quarters were females, and most of the headaches were recurrent (56.9%), severe (62.4%) or had associated red flags (78.0%). Computed tomography (CT) and magnetic resonance imaging (MRI) were the only scans adopted (4:1 and 1:1 for first and repeat scans, respectively). Twelve (11.0%) scans had findings likely to explain the headaches after the initial scans, with no difference in findings between diagnoses from CTs and MRIs (P = 0.41). Repeat scans offered no additional benefits, and roughly one in three patients were referred to third-party carers (mostly neurologists). Females had more recurrent headaches (OR = 2.63; CI = 1.09–6.35; P = 0.03). Patients with psycho-morbidities were less likely to have scan findings that explained their headaches (OR = 0.22; CI = 0.06–0.88; P = 0.03), and, though not quite significant, were also more likely to undergo imaging (OR = 1.47; CI 0.96–2.27; P = 0.08). Conclusion. Significant intracranial findings were uncommon following imaging for headaches, and MRIs offer no advantages over CTs. Repeating head scans within 5  years offers no clear benefits. Psycho-morbidities should be considered when deciding the imaging needs, given the lesser chance of findings. Larger studies will help validate these findings.