Killoughery, a left winger, joined Torquay United as a trainee on 1 July 2001, having been spotted by Torquay youth coach Richard Hancox playing, alongside another future trainee Biju Kironde, for Lewisham against Exeter City in an FA Youth Cup match.
His league debut came while still a trainee, on 29 March 2003 when came on as a late replacement for Simon Clist in the 1-1 draw at home to Boston United.
[2] He made a further appearance as a substitute against Southend United[3] the following month and two days later started the 2-2 home draw with Leyton Orient.
[4] In the 2003 close season, Killoughery, along with four other trainees (Kain Bond, Lucas Burgess, Ben Camara and Steven Orchard) signed professional with Torquay.
His final first team appearance came on 14 October 2003 when he was a second-half substitute for Jason Fowler in the Football League Trophy defeat away to Peterborough United.