Sydney Boys High School is proud of its long standing community partnership with the Centennial Park and Moore Park Trust .

Sydney High was originally granted access to an area in the Centennial Parklands by the NSW government in 1928. This followed the need to provide playing fields for a government school located on a confined site in the Centennial Parklands precinct. This need still exists today.

Following the granting of access, the Sydney High community began the transformation of what was a swampy area of the parklands into the McKay playing fields. Subsequently, in 1933, the Sydney High community built the Fairland Pavilion and extended the facility in 1952. Both the Fairland Pavilion and McKay Oval are named after the High old boys who led the development of the facilities. The previous refurbishment of the Fairland Pavilion includes the donation of an electronic scoreboard in memory of High parent and rugby supporter Richard Green. A further upgrade and refurbishment of the Fairland Pavilion is now urgently required to secure a further 20 years of continued access.

The partnership between the Centennial Park and Moore Park Trust and Sydney High, through the AAGPS sporting competitions in rugby, football, cricket,  athletics and cross country, has borne witness to the sporting history of  Sydney. High has participated in the AAGPS sporting competitions since 1906 and many New South Wales and Australian representatives from High and other schools commenced their careers in sporting events conducted using the McKay and Fairland facilities.

Sydney High’s use of the Centennial Parklands draws in many visitors who may otherwise not access the park . This includes not just High students and their families but also the students and families of other government and private schools from around Australia against whom High competes. Most of these schools are located outside the Eastern Suburbs.