Caulfield spent the majority of his playing career at Cork City and was a member of the team that won the 1992–93 League of Ireland Premier Division.

Caulfield has also played Gaelic football and represented both Roscommon and Cork at inter-county level, winning an All-Ireland title with the latter.

In 1983–84, together with Turlough O'Connor and Fran Hitchcock, he was a member of the Athlone Town reserve team that won the League of Ireland B Division.

He also made his first senior League of Ireland appearance with Athlone Town, coming on as substitute against Home Farm on 27 October 1985, making what Caulfield himself described as a "three-minute" debut.

[12] While playing for Cork City, Caulfield continued to live in Ballineen and Enniskeane where he started a family with his wife, Grainne.

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.

[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] While still playing for Cork City, Caulfield began attending FAI coaching courses and was tutored by, among others, Brian Kerr.

He also coached the West Cork Schoolboys League representative team that played in the Kennedy Cup at inter-league level.

In the 2016 FAI Cup Final, City won when Sean Maguire scored a last minute extra time goal against Dundalk.

[28] In the 2016–17 UEFA Europa League Caulfield guided City to the Third Qualifying Round, defeating Linfield and BK Häcken before losing out to K.R.C.

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.