The histories of literary sports journalism are marked by similar features. With a view to presenting past developments and providing a lens to reflect on the impact of current and nascent changes, literary football writing is positioned here as an exemplar. One that highlights where the literary journalistic reports produced between the 1930s and 1950s were overwhelmed by the rise of the tabloid media in the late 1960s and early 1970s, only for alternative often literary football perspectives to re-emerge on the terraces in the 1980s in the football fanzine. These handmade publications, which echoed the handmade papers sold in the early parts of the century, were sold outside football stadiums and led directly to the emergence of literary forms of football writing in the early 1990s. In the last decade of the twentieth century, football writing experienced a cultural embourgeoisement. Now, in the third decade of the twenty-first century, the throughlines of its early literary journalistic influences are echoed and illustrated across the form, even as it experiences another and arguably more significant cultural shift. In unpacking key aspects and important writers of literary football writing, this chapter foregrounds and foreshadows, maps and exemplifies, the book’s broader discussion.