Three years later, O'Rourke clinched the FA Cup with Bradford in 1911, beating Newcastle United 1–0 in a replay.
His son, Francis, died in Newfoundland in October 1919, affecting him deeply, and in June 1921, due to ill health, O'Rourke retired from the game.
In December of that year, O'Rourke joined Dundee Hibernian, who were then a non-league club, but stayed for only three months, resigning after lacking financial support.
He spent just ten months at Park Avenue but signed another son, Peter, who scored twice on his debut against Durham City.
After retiring, O'Rourke returned to Bradford living in Burlington Terrace next to City's Valley Parade ground until he died in January 1956 at the age of 82.