The race was first held on Thursday 13 June 1872 and was won by a horse called Prior who won by 20 lengths. It was called the Warrnambool Handicap Steeple until 1877, the Grand National Steeple from 1878 to 1881, the Warrnambool Handicap Steeple again until 1894, and has had the current name of the Grand Annual Steeplechase since 1895.

The distance is listed as about 5500 metres because sections of the race are run in open paddocks without fences. It is the longest horse race run on an Australian racecourse and has 33 obstacles, which is more than any other steeplechase in the world.

Multiple winners: Gold Medals (2018 & 2021); Regina Coeli (2015 & 2017); Al Garhood (2010 & 2011); Hibernian Prince (2001 & 2002); Hoki (1995 & 1996); Commission Red (1990 & 1991); Thackeray (1979 & 1980); Blueholme (1972 & 1974); McKenna (1958 & 1959); Napier (1906 & 1907); Peveril (1896 & 1897); Macduff (1892 & 1893); Native (1889 & 1890); All Serene (1883 & 1884); Greystanes (1878 & 1880).

Fastest time (5500m): Hoki (1996) 6:38:4

Winners of past Warrnambool Cup include Gunnamatta (2003), Placido (1994), Dandy Andy (1988), Nicholas John (1985), Puramaka (1977 & 1978), Scotch And Dry (1974) and Glenvue (1951 & 1954).