Holy Cross College, Woollahra, was established in the newly formed parish of Holy Cross by Cardinal Moran and the Parramatta Sisters of Mercy in 1908 as a select high school for middle class Catholic girls in the northern section of the Eastern Suburbs of Sydney. Moran made it clear, and it was obvious that the sisters agreed, that the primary purpose of the College was the imparting of the Catholic Faith integrated with a suitable middle class education equal to, but preferably excelling, that provided by the secular state schools. This thesis is informed by two questions: Why did Holy Cross College close in 2001? Did the College achieve the objectives of the founding pioneers of the school, including Cardinal Moran? This strongly contextualised thesis demonstrates that for almost a century Holy Cross College was a microcosm of a complex world, one which was influenced by many factors, at local, state, federal and international levels. These factors, in the early days, included the rapid response of Catholic educators to Peter Board’s ‘New Syllabus’, the first wave women’s movement; and the dubious rationalising argument of Cardinal Moran to extract aid for Catholic schools from the state, which remains an ongoing problem for Catholic education in Australia. While the College in the 1920s was enjoying a growing reputation for highly successful music and academic tuition, it was challenged, through to the 1950s, by such factors as: Pope Pius XI’s call to Catholic Action as interpreted for the Archdiocese of Sydney by Archbishop Kelly; participation in the various public displays of Catholic faith; the rigours of the Great Depression; and the dangers of being in an especially vulnerable location during World War Two. The community of the College which inhabited this complex ‘mini’ world was strongly bonded by common goals and values for the first fifty years of the school’s existence. This was a community which aspired to the fullest possible development of the spiritual, intellectual, cultural and physical attributes of girls through a Catholic education inspired by the Mercy Vision, but always constrained by the reality of finances, staffing, physical resources, and imposed authority. The somewhat idyllic existence of the College with its relatively small numbers and homely atmosphere was disrupted in the 1960s when Holy Cross was selected by the Sydney archdiocesan educational authorities to be a regional school. This study reveals the increasing complexity of the various levels at which authority was exerted over Holy Cross College as a regional school. Regionalisation was a central element in the Sydney Archdiocese’s wide ranging plan to cope with the enormous strains on the Catholic educational system caused by such post-war challenges as the influx of Catholic migrants and the implementation of the Wyndham comprehensive secondary education scheme. There followed the success of the state aid campaigns and the challenges of Vatican II Council, movements which impacted upon the personal and communal lives of the women religious who staffed the College, as well as their students. Also impacting upon the College was the cultural revolution and the second wave women’s movement of the 1960s and 1970s. Throughout this study the geographical setting of the school in Sydney’s Eastern Suburbs and the region’s socio-economic characteristics are explored and emerge as significant factors in both the creation and maintenance of a unique school culture and the decline of Holy Cross College in the 1990s. Finally this decline is mapped in terms of the erosion of the College’s unique identity, which was forged by religious, cultural, geographical, political and pedagogical forces, and eroded by a complex of factors including demography, centralised authority, class, and international economic downturns. It is concluded that the founding sisters and Moran would have mixed and nuanced responses to the question: Did the College achieve the objectives of the founding pioneers?