The aim of this article is to create a space for historical thinking in medical practice. To this end, we draw on the ideas of R.G. Collingwood (1889–1943), the renowned British philosopher of history, and explore the implications of his philosophy for clinical medicine. We show how Collingwood's philosophy provides a compelling argument for the re-centring of medical practice around the patient history as a means of restoring to the clinical encounter the human meaning that is too often lost in modern medicine. Furthermore, we examine how Collingwood's historical thinking offers a patient-centred epistemology and a more pluralistic concept of evidence that includes the qualitative, narrative evidence necessary for human understanding. We suggest that clinical medicine can benefit from Collingwood's historical thinking, and, more generally, illustrates how a philosophy of medicine that draws on diverse sources from the humanities offers a richer, more empathetic clinical practice.