He is a former Irish footballer who played for Galway United, Shamrock Rovers (over two spells), Reading, Accrington Stanley, Cork City and Shelbourne.
[7] He picked up his first senior trophy, playing all five games and scoring three goals en route to winning the 2011 Setanta Sports Cup.
Sheppard earned the penalty late in extra time that saw Rovers win through 3–2 on aggregate away to FK Partizan in the 2011 Europa League Playoff Round.
On 12 January 2012, Sheppard announced via Twitter that he had signed a two-and-a-half-year contract at Reading, leaving Shamrock Rovers on a free transfer.
[17] He made his return to the team in a 1–0 defeat to Coleraine on 11 February in the Setanta Cup,[18] but had to wait nearly three months for his first goal, scoring a late equaliser in a 1–1 draw with Sligo Rovers on 3 May.
Sheppard also represented his country at U17 level where he scored after coming on as a substitute at Terryland Park in a 2008 UEFA European Under-17 Football Championship qualifying round.
Sheppard made a substitute appearance for the League of Ireland XI in a 7–1 defeat to Manchester United in the first game to be played at the Aviva Stadium in August 2010.