Gilbert Ryle and R. G. Collingwood are not commonly associated with each other. From Ryle’s autobiographical essay (1971) we know that he saw Collingwood as an exact personification of pre-war Oxford: stuffy, hermetically closed off and philosophically dull; and, as did most of his analytically minded colleagues in philosophy, Ryle regarded Collingwood’s philosophy as a relic of past metaphysical theory. Collingwood, in turn, never paid any particular attention to Ryle’s philosophical writings, except on one occasion in 1935 when Ryle and Collingwood discussed their philosophical views with one another. At the time, Ryle was a lecturer at Christ Church College in Oxford and was already regarded as a promising philosopher, and Collingwood was Waynflete Professor of Metaphysical Philosophy. The tone in their brief correspondence was often biting and chilly, and the two philosophers seemed to disagree about almost everything. The correspondence between Ryle and Collingwood is discussed in the present article.