Kirrawee is part of the southern Sydney region inhabited by the Dharawal people at least 8,500 years prior to European settlement. Before being subdivided as Kirrawee, the area was part of Thomas Holt's Sutherland Estate and was accessed from Sutherland train station. In 1911 a tramway was opened, giving access to the area. At around the same time, the brickworks opened. In 1946, several blocks of land in Kirrawee went for several times their asking value - valued at £30, £60 and £64, they sold for £140, £195 and £160. As of 1949, the Department of Education had accepted a tender for a primary school to be built in Kirrawee. Some street names in Kirrawee commemorate colonial figures connected with the Rum Rebellion: Bligh Street and Putland Close were named after Governor William Bligh, and his daughter, Mary Putland, respectively; Johnston Avenue was named after George Bain Johnston, a First Fleet lieutenant who arrested Governor Bligh; Kemp Avenue was named after Anthony Fenn Kemp, a captain in charge of government stores who was also involved in Bligh's arrest. In February 1966 Kirrawee High School opened. In that same year, the Housing Commission built low-cost fibro homes in Kirrawee. In October 1968, bushfires went close to Kirrawee and residents prepared to evacuate, but the fire was brought under control.