Boxing’s presence in and contribution to the development of literary sports journalism is rarely over-estimated. Through textual analysis, this chapter examines the work of three key historical exponents, Pierce Egan, AJ Liebling and Hugh McIlvanney, whose work provided templates for writing on other sporting forms. Egan adopted a fashionable, flamboyant and slang-filled style, known as ‘the flash’, in his coverage of illegal prizefights, first for the Weekly Dispatch and then for his own publications, Boxiana and New Boxiana (1812–1829) (Snowdon, Hazlitt’s Prizefight Revisited: Pierce Egan and Jon Bee’s Boxiana-Style Perspective. Romantic Textualities: Literature and Print Culture, 1780–1840, (20) (Winter 2011). https://www.romtext.org.uk/articles/rt20_n02/ , 2013a). Described as ‘the most quotable wit ever by-lined’ (Randall, The Great Reporters. Pluto Press, 2005), The New Yorker writer, AJ Liebling, frequently cited Egan’s work and self-consciously developed his own version of the flash style. Inspired by Liebling’s book, The Sweet Science (1956/2018), Hugh McIlvanney was one of the great stylists of British sports writing—the only writer to win Sports Journalist and Journalist of the Year awards (Hoey & McGowan, Don Davies & Hugh McIlvanney: Literary Football Reporters Who Elevated British Sports Journalism, in, McGowan, L. & Symonds, K. (Eds.) Intersections of Sport and Society in Creative Writing. (pp. 31–46). Springer Nature, 2023). Across a span of more than 160 years, these three writers can be seen as the leading architects of literary journalism about boxing. In examining their histories, this chapter provides a cornerstone for our definitions of contemporary sports literary journalism.