Reid started his career at Coventry City's youth academy in 2000, spending two years at the club before opting to join Ipswich Town in 2002.
Reid signed for Conference Premier club Grays Athletic on a short-term deal in August 2008, before being loaned out to Newport County.
Reid left Harriers by mutual consent early in the 2015–16 season, and then spent brief periods at various levels of non-League football with Brentwood Town, Lincoln City and Gainsborough Trinity.
[14] Reid signed for Conference Premier club Grays Athletic on a one-year deal in August 2008, making his debut in a 1–0 home loss to Eastbourne Borough.
[18] Reid scored four times in ten league appearances during his loan spell at Newport,[19] before signing for the club permanently on 19 December 2008.
[30] During the January 2011 transfer window, it was reported that Reid had attracted interest from Premier League club Stoke City, as well as from his former employers, Coventry.
[30] He scored his first goal for the club in a 2–1 away victory against Oxford United on 15 March, running onto Rob Sinclair's through pass to give Stevenage the three points.
[30] Reid started the first competitive game of the 2011–12 season, on 6 August 2011, playing 70 minutes in a 0–0 draw at home to Exeter City, before being substituted for Byron Harrison.
[43] His fourth goal in five games was Stevenage's first in a 5–1 victory against Sheffield Wednesday on 13 September 2011; he reacted quickest to a parried Michael Bostwick shot and scored from six yards out.
[46] Reid went on to score goals in home victories against Brentford and Bury,[47] with the latter strike coming in a 3–0 win that ultimately secured Stevenage's place in the play-offs.
[36][51][52] He made his debut for the club on the opening day of the season, playing the whole match as Aldershot lost 7–6 on penalties to Wolverhampton Wanderers in the League Cup.
[55] He added a further three goals to his tally before the end of 2012, and opened the new year by scoring the winner from the penalty spot in a 1–0 victory away at Barnet, his tenth of the season.
[52] Although Aldershot did not initially release Reid, his contract was cancelled by mutual consent, and on 1 August 2013, he returned to League Two when he signed a one-year deal with Southend United.
[52] Southend manager Phil Brown stated that he hoped Reid would replace the goals scored by strikers Gavin Tomlin and Britt Assombalonga, both of whom had left.
[58] Reid made his Southend debut two days after signing for the club, on 3 August 2013, coming on as a 68th-minute substitute in a 1–0 victory against Plymouth Argyle.
[61] The move meant that Reid would be reunited with manager Graham Westley, who had signed the player for his first spell at the club three years earlier.
[62] Reid made his Kidderminster debut on the opening day of the 2014–15 season, playing the first 64 minutes of the club's 0–0 draw away at Lincoln City.
[71] He signed for another National League North club on 6 June 2016, Gloucester City, managed by Tim Harris who was director of football at Newport when Reid was playing there.
[72] Reid made his debut for Gloucester in the club's first match of the 2016–17 season, playing the opening 84 minutes in a 1–1 draw away at Salford City.
[78][80] Following his release from Newport, Reid returned to his home city to join Midland Football League Premier Division club Coventry United.
[86] Reid was not named in Coventry United's squad list ahead of the 2018–19 season as he began to focus on earning his coaching badges.
[75] After signing Reid for a third time, Westley stated "pace was never his main attribute which is why, four years on, I am comfortable that he can still play a role in what we do next.