The game of baseball and the diamond upon which it is played function within North American society to stabilize settler colonial identities and processes. This paper draws on ethnographic research of the Field of Dreamers Cooperative Softball Association in Toronto, Ontario, to explore how this recreationalsoftball league attempts to create radical spaces of play within, against, and beyond the dominant power structures that govern social relations in a settler colonial context. This study describes the practices and processes by which the league works to unsettle their spaces of play from the national myths of baseball history and settler futurity. It also reflects on the Field of Dreamers’ endeavors to create relationships and practices that acknowledge the territories on which they play while disrupting social relations that often exclude people from organized sports and public space.