We investigated the association between clinical rotation at a specialized headache center and headache knowledge of resident trainees. Using standardized pre- and post-questionnaires, change in self-reported knowledge of headache disorders and management in 31 participants undertaking clinical rotations were evaluated. There was a statistically significant improvement in self-reported measures of headache disorder knowledge post-rotation [mean score (SD), 3.19(0.543), p < 0.001] and significant improvement in overall knowledge measured using case-based questionnaires pre- vs. post-rotation [7.1(1.4) vs. 7.9(1.5), p = 0.003]. Rotation at a specialized headache center improved trainees’ self-reported knowledge and test-based scores, suggesting that such rotation should be included in postgraduate curriculum.