O'Reilly won a scholarship to the Sydney Teachers College at Sydney University, to train as a schoolmaster. However, the financial assistance was only for two years and merely sufficient for O’Reilly’s rent at Glebe Point. When he was in Sydney, O'Reilly received an invitation to join an athletics club based on his performances in Goulburn, but was only able to join after the secretary Dick Corish waived his membership fee. Jumping 47 feet, he came second in a triple jump competition behind Nick Winter, who went on to win gold in the event at the 1924 Summer Olympics with a world record of 50 ft. O'Reilly also placed second in a high jumping competition, clearing six feet. Corish was also a cricket administrator and invited O’Reilly to play in a David Jones Second XI. Not knowing anything of his new recruit’s abilities, Corish did not allow O’Reilly to bowl until he explicitly complained of only being allowed to field. O’Reilly promptly finished off the opposition’s innings by removing the middle and lower order. After an encounter with journalist Johnny Moyes, who wrote glowingly about O'Reilly's skills.
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