This book argues for the value of reading Peter Winch (1926–1997), one of the important philosophers of the 20th century and known especially for his work on Wittgenstein and the philosophy of the social sciences, paired with R. G. Collingwood (1889–1942), famous for his philosophy of history. Both Winch’s and Collingwood’s seminal works made a deep impact on debates on the aims and methods of the human sciences. Moreover, their similarity on those topics rested on a shared vision of philosophy in general. This is the first book-length treatment of the two philosophers together. The authors make use of untapped manuscript sources and posthumous material published only in the last decades to show that Winch and Collingwood were much closer than expected and to lay to rest some pervasive misunderstandings. Underneath their shared views on the autonomy of the human sciences was a contextualising approach to logic, language and metaphysics. An accessible articulation of Winch’s and Collingwood’s thinking on key points, this volume is valuable reading for students and scholars interested in the philosophy of history and social science, presenting a vision of philosophy as an intellectual and existential pursuit.