O'Rourke started his career with Airdrieonians, moved to Albion Rovers, before moving back to Airdrieonians, for whom he won a Division Two title winning medal. He won his one and only cap for Scotland scoring against Ireland on 16 March 1907 before a month later signing for Bradford City. He had been playing at Valley Parade in a friendly for Airdrieonians after which the City board woke him from his hotel room in Leeds to sign. He scored on his debut on 6 April 1907 in a 2–1 defeat to Nottingham Forest, two in his second game and a fourth goal in his third. He finished as top goal-scorer with 21 goals in 1907–08, one ahead of strike partner Wallace Smith, including four in a 7–1 victory over Gainsborough Trinity as City won the Second Division title. He was again top goal-scorer the following season with 19 goals as he played in every game for City, who stayed up on goal average from Manchester City. He was again top goal-scorer in 1909–10thanks to three goals in the FA Cup, although he was one goal behind Robert Whittingham in the league. The club's league position of seventh was beaten in 1910–11 as City came fifth, the club's highest league finish, with O'Rourke scoring 13 goals. The season also saw City win its only piece of major silverware in its history when it defeated Newcastle United in the 1911 FA Cup final. O'Rourke scored just one goal in the run to the final when he netted the first goal in the 3–0 semi-final victory over Blackburn Rovers. The first game of the final had finished 0–0 with the only goal of the replay being scored by captain Jimmy Speirs. Some sources has credited the goal to O'Rourke, but he denied touching the ball. O'Rourke was now 32 and his games and goals dried up, as he made just 46 more appearances in the final four seasons before the First World War netting 11 goals. But his final tally of 88, from 192 league appearances, stood as a club record for 69 years when Bobby Campbell broke it in October 1984 on his way to 121 club league goals. His playing contract was terminated in September 1922, though his last league game came in 1914. He remained as first-team trainer until 1926 before he retired to his birthplace, Bargeddie, where he died on Christmas Eve 1954, aged 77.
