He was spotted by Manchester City who offered him a one-year YTS deal while playing for Stella Maris.
He became a regular for City's youth and reserves teams alongside the likes of Shaun Wright-Phillips.
He was a regular in the Halifax team during his time at The Shay but when his contract expired, he decided to return to Ireland.
Upon returning to his homeland, Reilly signed for Stephen Kenny's Bohemians and made his debut in a 1–1 draw with Cork City on 1 November 2002.
He made numerous appearances during the 2002–03 season as Bohs won the League of Ireland Premier Division.