Born in Stourbridge, West Midlands,[1] McDermott progressed through the Walsallyouth system and he earned a scholarship place ahead of the 2004–05 season.[2] He made his first team debut in a 1–0 defeat to Sheffield Wednesday in the League Cup after entering the game as a substitute in the 77th minute on 25 August 2004, which was his only appearance of the 2004–05 season.[3] He finished the 2005–06 season with three appearances and he signed his first professional contract with Walsall in May 2006.[4][5] He joined Southern League Premier Division club Halesowen Town on an initial one-month loan on 4 January 2007,[6] where he made four appearances and scored two goals.[7] He finished the 2007–08 season with 15 appearances for Walsall and he was released by the club on 7 May 2008.[8][9]
Kidderminster Harriers
He joined Conference Premier club Kidderminster Harriers on a free transfer in August following a trial.[10] He made his debut in a 1–1 draw against Lewes as an 80th-minute substitute on 9 August.[11] He finished the 2008–09 season with 29 appearances and one goal for Kidderminster and he signed a new one-year contract in July 2009.[12][13] McDermott was re-signed by Halesowen on an initial one-month loan on 17 February 2010 to try to regain full fitness.[14] He finished the loan in March with five appearances and two goals.[15] He was invited back to pre-season training by Kidderminster after he finished the 2009–10 season with 25 appearances and one goal.[16][17]
York City
He joined fellow Conference Premier team York City on trial in July 2010 and he played in a 1–0 pre-season friendly defeat to Hull City, with managerMartin Foyle saying he was impressed by McDermott's performance.[18][19] Ahead of the 2–0 friendly defeat to Barnsley in which McDermott featured,[20] Foyle spoke to the player's agent ahead of deciding over offering him a contract.[21] After scoring from a "weakly struck" direct free kick to score the winning goal in a 1–0 friendly victory over Morecambe,[22] McDermott was offered a contract with York and he signed for the club on 28 July 2010.[23][24] He made his debut as an 82nd-minute substitute in a 2–2 draw at Bath City on 21 August 2010.[25] Having made four appearances for the club, McDermott was released by York on 5 October 2-1- before being re-signed on another month-to-month contract on 19 October by new manager Gary Mills.[26][27] His first appearance since returning was in a 2–0 victory at Kidderminster in the FA Cupfourth qualifying round on 23 October 2010, which was also his first start for York.[28] McDermott scored his first goal for York in a 2–0 victory over Southport on 23 November.[29] He agreed a new contract with York on 27 December 2010 that would keep him at the club until the end of the 2010–11 season, which would be signed in January 2011.[30]
Despite having yet to agree terms on a new contract he was invited back to pre-season training with York,[31] before re-signing on non-contract terms on 1 July 2011.[32] He suffered a foot injury during a 1–1 draw with Garforth Town in pre-season on 11 July 2011, which required an X-ray.[33] By October 2011, Mills was looking to loan McDermott out in order for him to play regular first team football.[34]