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Later life:
O’Callaghan remained with Deane and Woodward’s practice for a further 12 years. During this time, he married his wife Eva Higgins in 1869 in a church in Rathmines. Two years after his wedding, he created an office for himself which was situated on 16 Nassau Street, Co. Dublin in 1871. For the first thirty years of O'Callaghan's practice, he did not have a partner. His practice received many contracts for Roman catholic churches, church schools, and convents. These contracts include St. Joseph’s church in Clifden and the O’Brien Institute Clontarf. In 1872 O’Callaghan became the first ever president of the Architectural association of Ireland to be elected. A notable moment from his time as president of this association is a lecture that he had given on the education regarding future architects. Later on in O’Callaghan’s presidency he presented papers on the importance of students paying more attention when it came to learning how to measure and study ancient buildings. In 1880 O’Callaghan obtained the contract for the O’Brien Institute through winning an architecture competition with two illustrations had submitted. The work commenced in 1880 and was finished in 1883. In the same year, O'Callaghan won another architecture competition for the contract of a Hospital of the Holy Ghost in Co. Waterford. In 1888 O'Callaghan participated in a competition to build a chapel for St. Patricks College Maynooth but did not win. One of O'Callaghan's final contracts was received in 1902 for St. Finian's College in Mullingar. He did not see the completion of this project as he suffered from a decline in health during the final years of his life and died on the 5th of November in 1905 at the age of 67.