Headache is a rare yet clinically significant presentation of ischaemic heart disease (IHD). While chest pain is the hallmark symptom of myocardial ischaemia (MI), some patients present with atypical symptoms, such as headaches, which lead to diagnostic challenges and potential delays in treatment. This case series highlights the diagnostic complexity and clinical significance of headache-predominant presentations of both acute and chronic coronary syndromes, emphasizing the need for a comprehensive differential diagnosis in patients with cardiovascular risk factors. We present two cases where headache was the primary symptom of MI. The first case describes an acute ischaemic event wherein the headache preceded the onset of classic cardiac symptoms, leading to the identification of an occluded obtuse marginal artery. This was the second case in our institution where a previous patient presented with exertion-induced headaches, ultimately diagnosed as a chronic total occlusion of the left anterior descending (LAD) artery, which was successfully revascularised. Two years later, the same patient re-presented with acute coronary syndrome secondary to disease in a different coronary artery and his presentation was solely with headache. Both cases were successfully managed with percutaneous revascularisation, resulting in the resolution of symptoms and reinforcing the link between headache and CAD. These cases underscore the importance of considering ACS and chronic stable angina in patients presenting with unexplained headaches, particularly when symptoms are exertional or pressure-like. Early cardiac assessment, including ECG and further imaging when indicated, is essential for timely intervention. Raising the awareness of exertional headache as a potential ischaemic symptom may facilitate earlier diagnosis and prevent adverse outcomes. Further research is required to elucidate the mechanisms underlying headaches in MI and refine diagnostic approaches for atypical cardiac presentations.