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.
Longford Town
After ten seasons he transferred to Longford Town for one season.
Cork City
He then signed for Cork City where he again spent only one season.
Shamrock Rovers
Reynolds then joined Shamrock Rovers. He made his debut on 11 April 2003 against Drogheda United[3]
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.
Player/Manager at Waterford
In March 2004 he was appointed player-manager at Waterford United with Paul McGrath as Director of Football. The Blues reached the FAI Cup Final in his first season before disastrously losing the game in the last five minutes.
Shelbourne
He resigned in March 2005 before joining Shelbourne making his debut in August and winning the League that season.
Rejoining Waterford
In July 2006 he rejoined Waterford United. He left the club exactly one year later in July 2007.
Rovers return
He made his second debut for Rovers on 6 July 2007 at Longford.[4] In total he made a combined total of 40 appearances without scoring in his two spells at Rovers.
Management/Coaching Career
Derry City
On 10 January 2008, Reynolds was appointed Assistant Head Coach at Derry City.[5]
On 30 January 2016, Reynolds was appointed Assistant First Team Coach of Cork City. He spent one season at Turners Cross before leaving for his native Waterford. He helped the rebels in a win over Dundalk at the FAI Cup with a 1–0; he had just place after the same team in the Premier Division.
Return to Waterford
Again, Reynolds was appointed as Waterford manager on 2 January 2017, working alongside Director of Football Pat Fenlon. He was given the allowance to sign some top League of Ireland players such as Kenny Browne, Paul Keegan and Mark O'Sullivan to name a few. The side achieved promotion at first opportunity, Waterfords 3–0 win over Wexford coupled with nearest challengers Cobh Ramblers 3–0 defeat to Cabinteely secured the First Division title with two games to spare and for the first time in ten years his hometown side were in the League of Ireland Premier Division due to his guidance.[6]
In July 2021 Reynolds was named as assistant manager of the Reoublic of Ireland U21 team under manager Jim Crawford.[8] On 5 August 2024, Reynolds departed his post as assistant manager, following criticism from Bohemians fans that he was not fully committed to his post as Bohs manager.[9][10]
In April 2023, it was announced that Reynolds had left Derry to return home to Waterford, where he would become assistant to new Waterford manager Keith Long.[15]
Bohemians
Reynolds was appointed manager of Bohemians in March 2024.[16] He drew criticism from Bohs fans following a 2–1 defeat at home to Derry City on 13 June 2024, for missing the preparation for the game by spending a week in Croatia with the Republic of Ireland U21 side as part of his role as assistant manager, when it emerged that he was remaining on in that role alongside his club commitments.[17] He then stepped down from his Ireland U21 assistant manager role on 5 August 2024.[18]