While training as a teacher, O’Reilly joined the Sydney University Regiment, a unit of the Militia Forces (Army Reserve). He did not enjoy his time in the military, and along with most of his peers, regarded the commanding officer as inept. O'Reilly was a non-conformist who did not enjoy taking orders, and was unimpressed with the firearm drills, because the recruits were armed only with wooden sticks. However, he signed up for a second year to raise money for his education. Fed up with military routines he considered to be pointless, O'Reilly volunteered to be a kitchen hand.
During a vacation, O'Reilly caught the train from Sydney back to Wingello, which stopped at Bowral mid-journey. There, Wingello were playing the host town in a cricket match, and O'Reilly was persuaded to interrupt his journey to help his teammates. This match marked his first meeting with Bowral's 17-year-old Don Bradman, later to become his Test captain. O'Reilly himself later described thus:
How was I to know that I was about to cross swords with the greatest cricketer that ever set foot on a cricket field ? ... by the close of play, 17-year-old Don Bradman was 234 not out. The match resumed a week later, according to the local custom ... I bowled him first ball with a leg-break which came from the leg stump to hit the off bail. Suddenly cricket was the best game in the whole wide world.
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