The first sporting contests between the two schools date back to 1863 – informal games played on Saturday mornings at the Commun na Feinne Reserve in South Geelong.

Bert Keith and George Notman note in The Geelong College 1861-1961, when Grammar reopened in 1863, it “soon provided new opportunities for trials of strength,” and a rivalry quickly grew.

In 1868, the two schools combined to beat the Geelong Football Club, highlighting the unique nature of their rivalry. In his history of Geelong Grammar School, Light Blue Down Under, Weston Bate explained that “an epic quality was built into the rivalry” in 1878 when, after playing two draws, popular demand forced the schools to play a decider at the Corio Oval (then home of the Geelong Football Club), which also ended in a draw. Bate said that “the College match was always the match of the year” and that “when they weren’t arguing about the eligibility of players” the games were “usually close, hard-fought encounters”. They were also among the most popular and well-attended sporting contests in Geelong. So popular that in the 1920s, admission was charged to fundraise for local charities, particularly the Red Cross.

In recent years, Derby Day has celebrated all APS Winter Sports, with games played between Grammar and College on netball courts, hockey and soccer pitches, as well as football ovals.