He made his League of Ireland debut on 1 December 1991 for his hometown club Waterford United under the stewardship of Alfie Hale. His first goal for the Blues came on 21 November 1993.
After ten seasons he transferred to Longford Town F.C. for one season before arriving at Cork City F.C. where he again spent one season before joining Rovers. He made his debut on 11 April 2003 against Drogheda United
In his first season in the Hoops he played in four European games, including the famous UEFA Intertoto Cup win in Poland over Odra Wodzisław.
In March 2004 he was appointed player-manager at Waterford United with Paul McGrath as Director of Football in March 2004. The Blues reached the FAI Cup Final in his first season before disastrously losing the game in the last five minutes.
He resigned in March 2005 before joining Shelbourne F.C. making his debut in August and winning the League that season. In July 2006 he rejoined Waterford where he remained until July 2007 after parting company by "mutual consent".
He made his second debut for Rovers on 6 July 2007 at Longford . In total he made a combined total of 40 appearances without scoring in his two spells at Rovers.
On 10 January 2008, Reynolds was appointed Assistant Head Coach at Derry City FC.