Reid went on to begin his senior football career in Australia for Wollongong Wolves in 1998. He became a cult hero during his time at the Wollongong Wolves after scoring the last minute equaliser in the 2000 grand final against Perth Glory. The Wolves went on to win the game 7–6 on penalties. In 2002, Reid moved to England and joined Bradford City, but only stayed for one season before joining Brighton & Hove Albion in 2003. Reid had usually played in the right-back position in defence for the Seagulls, but the player has stated his preferred position is in the centre of midfield. Near the start of the 2006–07 season, Reid suffered a serious knee injury which saw him sidelined for nearly a year, but the player did return for the start of the 2007–08 pre-season. On 6 May 2008, it was confirmed that Reid, along with experienced trio Kerry Mayo, Gary Hart and Guy Butters were to be released from the club. On 11 July 2008, Reid began training with Hereford United in a bid to win a new contract.
He was expected to sign with Perth Glory for the 2008–09 A-League season, but instead signed with Adelaide United on a two-year deal. He won a call up to the national-team squad in October 2008 along with Adelaide United teammates Scott Jamieson, Robert Cornthwaite and Eugene Galeković. Despite usually playing in a deep midfield role Reid has created a number of assists from both open play and set pieces. He scored his first goal for the club in a 1–1 draw against Wellington Phoenix at Westpac Stadium on 18 January 2009.
In early 2011, Reid had asked former club Adelaide United for a release to join hometown club Sydney FC for their 2011 Asian Champions League campaign, resulting in a bitter fallout between himself and then manager Rini Coolen who would not release him until season's end. In September 2012, it was announced that Reid was on trial with Sydney FC, taking part in two of their pre-season matches against A-League opposition before eventually signing a 1-year deal to join the Sky Blues beginning on 1 October 2012. However, as a result of Sydney FC failing to qualify for the A-League finals, Reid, along with teammates Nathan Sherlock, Krunoslav Lovrek, Trent McClenahan, Adam Griffiths and Jarrod Kyle were released by Sydney FC at the conclusion of the 2012-13 A-League season.
Rockdale City Suns
After being released as a player from Sydney FC, Reid signed for Rockdale City Suns in the NSW Premier League. However, he also still works for Sydney FC as a Community Football Officer.
International career
Reid made his senior international debut for the Socceroos on 28 January 2009 in an AFC Asian Cup qualifying match versus Indonesia.
Coaching career
Following Branko Culina departure from the managers position at Rockdale, following a poor start to the 2015 NPL, Reid was announced as Rockdale City Suns new coach, a position which he would combine with playing duty when required. Reid led Rockdale to the Round of 16 of the 2015 FFA Cup against A-League club Melbourne Victory at Jubilee Oval. Despite a valiant comeback, Melbourne would win 3-2 and go on to win the overall competition.