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Prior to commencing as Rector of Xavier College, Fr Middleton taught at St Aloysius College in Sydney, and later served as Chaplain at Newman College, the Jesuit residential college within the University of Melbourne, and then Vice-Rector at St Leo's College, within the University of Queensland.
In 1998 Fr Middleton was appointed Rector and Deputy Headmaster at Saint Ignatius' College in South Australia. In 2003 Fr Middleton was appointed Principal of St Aloysius' College. He taught History in Years 10-12 during his eleven years as Principal.
Fr Middleton also founded the Benenson Society, a human rights advocacy group. He was appointed a Province Consultor in 2011. In 2012 he was the Province Procurator and attended the Congregator of Procurators in Nairobi, Kenya. He completed his term as Principal in April 2014, and commenced as Rector of Xavier College in June 2014.