Career
McCaffrey spent his childhood in Clogher, County Tyrone, and he started his professional career with Scottish club Hibs. McCaffrey made only one appearance for the Hibs first team, in which he was sent official He was loaned out to First Division clubs Queen of the South and Livingston during his time with Hibs.
At the end of the 2007-2008 season, McCaffrey signed a three-year deal to play for Falkirk.
Having made only one appearance for Falkirk in over a year, McCaffrey joined Arbroath on loan on 18 September 2009. On 18 February 2010, British Broadcasting Corporation Sport reported that McCaffrey had agreed to return to Northern Ireland and his home town club, Dungannon Swifts.
McCaffrey signed for the club as an out-of-contract professional. McCaffrey signed for on 18 February 2012 McCaffrey has represented Northern Ireland at under-21 level