Philip Gillespie Bainbrigge is today best known for his friendship with Wilfred Owen in the last year of his life, but Bainbrigge is also an important figure in LGBT history. A brilliant classicist, poet, and sixth form master at Shrewsbury School, before his death in action on the Western Front, Bainbrigge looked back to the ancient world for models of love between males and of lesbian love, and he refused to apologise for the physical aspect of same-sex love. His surviving works were privately published after his death and include a Latin dialogue which tells the story of two schoolboys discovering the pleasures of sex together, and a riotously funny play, Achilles in Scyros: A Classical Comedy, which features cross-dressing by both men and women, a lesbian separatist chorus, and a devoted love affair between Achilles and Patroclus. This paper will explore extracts from both works and analyse their original contribution to LGBT history, which lies in their frank acceptance of and celebration of the sexual side of same-sex relations. The paper also places Bainbrigge in the context of a wide circle of homosexual friends, drawing on my research into unpublished letters, diaries, and poems.