He made a further substitute appearance on 3 May 2003, in a 1–1 away to Lincoln City and was awarded young player of the year and a professional contract that summer (along with fellow trainees Kain Bond, Lucas Burgess, Graham Killoughery and Steven Orchard).
In the 2003 close season, Killoughery, along with four other trainees (Kain Bond, Lucas Burgess, Ben Camara and Steven Orchard) signed professional with Torquay.
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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.
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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.
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