Career
He joined Cork F.C. in 1935 as an old fashioned outside right. The following year he was a runner up in the FAI Cup Final to Shamrock Rovers. However shortly afterwards he became embroiled in controversy when it emerged that, together with Owen Madden, he had signed for Norwich City before playing in the cup final on April 19.
When Cork F.C., who received no fee, protested over the moves, both O'Reilly and Madden were suspended by the FAI for three years. Played in a total of 5 Cup Finals scoring seven times. Scored twice in the 1941 FAI Cup final.
After retiring from the game Jackie emigrated to Canada.