Abstract. In this study, the problem of primary headache diagnosis is considered, referring to multiple frames of reference, including the complexity characteristics of living systems, the limitation of human information processing, the enduring nature of headache throughout history, and the potential for intelligent systems paradigms to both broaden and deepen the scope of such diagnostic solutions. In particular, the use of machine learning is recruited for this study, for which a dataset of 836 primary headache cases was considered, originating from two medical centres located in Turkey. Five primary headache classes were derived from the data obtained, namely Tension Type Headache (TTH), Chronic Tension Type Headache (CTTH), Migraine With Aura (MwA), Migraine Without Aura (MwoA), followed by Trigeminal Autonomic Cephalalgia (TAC). A total of 9 machine learning based classifiers, ranging from linear to non-linear ensembles, in addition to 1 random baseline procedure, were evaluated within a supervised learning setting, yielding highest performance outcomes of AUC 0.985, sensitivity 1, and specificity 0.966. The study concludes that modern computing platforms represent a promising setting through which to realise intelligent solutions, which in turn support the space of analytical operations needed to drive forward diagnostic capability in the primary headache domain and beyond.