The concept of the Foundation was driven by Robert Outterside, Headmaster 1977-1991, who had taught in the Mathematics Department of the School 1958-1960 and was well aware of the ethos of the School. After three years as Headmaster of Manly High School 1974-1976 he also understood the relationships between the Department of Education and its schools. Fundamental to the formation of the Foundation was the desire for the separation of decision-making powers untrammelled by Departmental imperatives.

The Sydney High School Foundation Inc. was established on 23 January 1986 and held its inaugural meeting 9 April 1987. The intervening year was spent on defining the separate roles and responsibilities of the Foundation and the, then, School Council which had existed since 9 July 1951 and managed the attendant facilities at Centennial Park and Abbotsford. The membership of the Management Committee of the Foundation includes the Principal, Presidents of the SHS Old Boys Union and the School Parents & Citizens Association along with three nominees from each of these bodies. The Foundation took over the administration of the Fairland Pavilion, the McKay Playing Fields and the Outterside Centre from the School Council shortly after it was established and continues the management, administration and maintenance on these facilities now.

Prior to 1951, the responsibilities taken over by the foundation were the roles of the OBU and the P&C through such bodies as the Rowing Committee established in 1924 and the McKay Sports Ground Committee in 1935. Foundation’s objects include acquiring, holding and managing real property on behalf of Sydney High School and entering into legal arrangements to preserve, develop and maintain facilities on behalf of the School. As an incorporated body it has the appropriate powers to carry out its objects.

It is important to note that there was an important link between those early committees, which had displayed considerable vision, and the present-day SHS Foundation Inc. That link was the formalised co-operation between the OBU and the P&C which was simply carried on under a corporate model.

In furtherance of its objects the SHS Foundation has an outstanding record of achievement which includes, inter alia: the establishment of the Foundation High Store and the purchase of a cash register with special software for an inventory system; the refurbishment of the original tennis courts; continued renovations of the Fairland Pavilion with funding assistance from parents and old boys; the finalisation of a Deed of Licence between the Foundation and the Centennial Park & Moore Park Trust; the completion of Stage II of the Abbotsford project with loan funds made available by The High Club; the creation of a Staff Computer Room; a joint venture with the Department of Education on the Senior Studies Centre and the later supply by the Foundation of air conditioning; and, the addition to the Outterside Centre of The Barris Cottage and the new pontoon.