Street railway strikes in the late nineteenth and early twentieth centuries were frequently the occasion for large-scale collective violence in North American cities and challenged the capacity of local authorities to maintain civic order. However, this was only the most visible manifestation of the challenge that street railway workers’ collective action posed to the order of liberal capitalism, an order constructed on several intersecting dimensions. Using the example of Canadian street railway workers from 1886 to 1914, a period of rapid urbanization and industrialization, this article explores the ways the collective action by workers and their community sympathizers challenged the workplace, marketplace, and “streetplace” orders of liberal capitalism. It discusses how those challenges were met through political and legal processes of resistance and accommodation, taking into account the fragmentation of state power, hostile public opinion toward the street railways, and conflicting views over the legitimate scope for workers’ collective action.