Ireland O'Keeffe began his career with
St Patrick's Athletic's youth system. In 2002, he joined the senior team and was loaned to
Kilkenny City in the
League of Ireland First Division. The following season, St. Patrick loaned O'Keeffe to
Dublin City for the first portion of the 2003 season. St. Patrick recalled O'Keeffe for the remainder of the 2003 season, and he debuted in the
League of Ireland Premier Division. St. Patrick's defeated
Longford Town for the
League of Ireland Cup throughout the season. He re-signed with St. Patrick's for the 2004 season and finished the campaign as the club's top goal scorer. O'Keeffe returned to play with St. Patrick's for the 2004 season but was transferred to league rivals
Bohemian during the summer transfer market. In 2007, O'Keeffe signed with
Drogheda United, where he helped the club win the league title. He participated in the
2007–08 UEFA Cup and played against
AC Libertas and
Helsingborgs IF. O'Keeffe also assisted the club in securing the
2007 Setanta Sports Cup, though he would miss the final after sustaining an injury. In 2008, he returned to Drogheda for his final season with the club. O'Keeffe was loaned for the remainder of the season to
Bray Wanderers. After the 2008 season concluded, he became a free agent.
Canada O'Keeffe ventured abroad to Canada in 2009 and played with the local side, the Toronto Celtic. He recorded his first goal for the club on May 15, 2010, against
TFC Academy. He would finish the campaign as the club's top goal scorer with 12 goals. He also helped the club secure a playoff berth by finishing third in the standings, just two points shy from winning the divisional title. O'Keeffe would contribute a goal in the semifinal round, where Hamilton advanced to the finals by defeating
Toronto Croatia. In the
championship finals,
Brantford Galaxy defeated Hamilton by a score of 3-0. == Honors ==