In 1902 a small group of sisters arrived in Southsea from Boscombe, Bournemouth to found an independent Catholic school for girls and small boys. It was established in Grove Road, Porstmouth and named Covent of the Cross after the school the sisters had left behind in Boscombe. During the Second World War, Portsmouth was heavily bombed and the women and children of The Convent of the Cross were evacuated to Gloucestershire. Meanwhile the buildings at Grove Road were used as a field hospital and were damaged by enemy action. Thus when the war came to an end it would have been very difficult to re-establish the convent. Oaklands is the name of a property comprising what is now known as the White House, plus eighty acres of land.

In the late 19th and early 20th centuries it was the home of General Napier. General Napier was a famous soldier who fought against Napoleon in the Peninsular War. He is most famous for the conquest of Scinde/Sind/Sindh now in Pakistan and for being Commander in Chief in India. Memorials to the family are to be found in St. Georges church, Waterlooville and the General is buried in the old Garrison Church in Portsmouth. There is also a statue of General Napier in Trafalgar Square and the city of Napier in New Zealand is named after him.During the 1920’s and 1930’s it was the home of another military man Colonel Williams.

In 1946 Oaklands was purchased by the sisters of The Convent of the Cross but it was in no fit condition for a school. For a while some of the sisters travelled to Southsea to teach the few students who were there. In 1947 when the school opened Stakes Hill Road was a lane with ditches on either side. The area and the school grew rapidly and in 1959 the junior department became a separate school under the name Holy Cross. In 1966 The Convent of the Cross amalgamated with another Portsmouth school, Daley’s, and became Oaklands Convent School. The Oaklands crest dates from this time.

The Havant area had become one of the fastest growing areas in the country with many new industrial estates including Leigh Park growing up. There became a desperate need to meet the educational requirements of a growing population. Land was purchased from the sisters for Crookhorn school and Purbrook Way and the money was used to finance the building of the gym and the hall block. But there was no provision for the education of Catholic boys in the immediate area. An approach was made to the new bishop, Derek Worlock and in 1971 Oaklands became a voluntary aided, mixed comprehensive for students from eleven to eighteen.

Since then the school has continued to grow. In 1971 a building project valued at half a million pounds was set in motion to provide for Maths, Science and Technology and to flatten the playing fields. Later purpose built blocks were built to house the Sixth Form and Year 11. There has also been in recent years the creation of a multi-gym, new Maths, R.E. and Technology classrooms and nine suites for Information Technology.

Other notable events have included a visit by the then Prime Minister, John Major, who spent several hours touring the school. In 1997 Oaklands celebrated its 25th year as a comprehensive school with family fun days and reunions of past students. To mark the Millenium and Jubilee 2000 the school commissioned a special setting of the mass which was based on a traditional Maori tune and arranged by Deputy Head Martin Lewis and music teacher Sian Bibby-Hsia.

In February 2003 the modular sixth form building was demolished to make way for a new purpose built block which was officially opened in November of that year by the Bishop of Portsmouth, Crispian Hollis. Shortly afterwards a new block for the music department was completed. In 2008 the John Paul II was completed to house the History, Geography and Bartimeaus (Learning Support) departments.

The school is now looking to the future in the hope that the ‘Building Schools for the Future’ initiative will provide funds for a new Maths, Science and Technology block to help continue the fine tradition of providing an excellent education for all its students.