The two-volume novel "Sinister Street" by Compton Mackenzie (1883-1972), a Scottish writer more famous now for his later comic novels, tends to be overlooked in the list of novels depicting English public school life. The first volume of Mackenzie's novel traces the protagonist's public school career at the nineteenth century's close. Despite the sensitivity required when dealing with fiction as a source for historical understanding, "Sinister Street" can shed useful light on public school life at a time of transition. Mackenzie's account is fictional but the experience of public school life within "Sinister Street" often chimes with reality, even though the chime may distort or mask much of what we know from historical record. In alluding to the march of an expanding middle class into the schools, the persistence of the gentlemanly ethos, the role of sports, and the tensions within the curriculum, the novel offers insight into the public school experience. It also illuminates the close of the nineteenth century, as events in the wider world impinge on the school and those who are part of it. "Sinister Street" is a useful source for historians of education in understanding the historical continuity and change that public schools underwent during this time.