Between 1986 and 2001, Caulfield played for Cork City, making his debut in a League of Ireland Cup game against Kilkenny City. Shortly after he scored the club's first hat-trick in a 3-2 win over Sligo Rovers on the 23rd of November 1986. Together with Pat Morley and Dave Barry, he subsequently became a prominent member of the City team that won the 1992–93 Premier Division, the 1997–98 FAI Cup, three League of Ireland Cups and eleven Munster Senior Cups. During this time Caulfield made 455 appearances for the club. This remains a club record. Caulfield is also the holder of several other club records including most starts (376) and most substitute appearances (79). Together with Pat Morley, he is the club's joint all-time top scorer with 129 goals.[3][7][8][9]
He was also the League of Ireland Premier Division Top Scorer in both 1991–92 and 1994–95.[10][11] In 2008, he was inducted into the club's Hall of Fame.[12]
While playing for Cork City, Caulfield continued to live in Ballineen and Enniskeane where he started a family with his wife, Grainne. They have two daughters, Sinead and Aideen. Throughout Caulfield's playing career with Cork City he maintained his amateur status and worked as a sale rep, initially with Bulmers and later for Diageo. He would continue to work for Diageo until he was appointed manager of Cork City in 2013.[9][7]
Gaelic football
As well as playing association football, Caulfield has also played Gaelic football at inter-county level. He initially represented Roscommon as a minor [8] but after moving to West Cork he played for St Mary's, Carbery and then for Cork at inter-county junior level.[2][9]
In 1990, he was a member of the Cork team that won the Munster and All-Ireland Junior Football Championships. In the All-Ireland final on September 9 at Páirc Uí Chaoimh he scored 1–3 as Cork defeated Warwickshire 3–16 to 0–8.[13] He continued to play for St Mary's until 2007 and was subsequently part of the coaching staff that guided the club to the 2009 West Cork Junior A Football Championship.[9][14]
Coach/Manager
Early years
While still playing for Cork City, Caulfield began attending FAI coaching courses and was tutored by, among others, Brian Kerr. He also began coaching schoolboy teams at Riverside Athletic, the Ballineen-based team that played in the West Cork League. He also coached the West Cork Schoolboys League representative team that played in the Kennedy Cup at inter-league level.[7][14]
In May 2019, Caulfield left his position as manager of Cork City after a disappointing start to the season in which the club picked up 13 points from their 14 league games.[32]
Galway United
In August 2020, Caulfield took over as manager of Galway United. United won the first five league games under his management as he guided the club to the promotion playoffs, however a loss to Longford Town saw the club remain in the Division for the following season. In 2021, after a sluggish start in which the club took just 9 points from the opening 9 league games, a strong finish to the season saw United finish 2nd behind Shelbourne. A home defeat to Bray in the playoffs saw the club again miss out on promotion. 2022 saw the club make the best ever start to a league season but a loss of form in the second half of the season resulted in a 3rd placed finish and another trip to the playoffs, this time Waterford FC ending the promotion hopes. He signed a new contract in September 2021 to bring him to the end of the 2023 season. The 2023 season saw them win the first division at the top with 94 points from 30 wins, 4 draws and only 2 losses for the entire season earning them promotion for the first time since 1994.[33]