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. In 2004–05 Avondale reached the
Munster Senior Cup. Caulfield was initially a player/coach at Avondale and in the semi-final he scored the opening goal in a 3–1 win over Clonmel Town. With Caulfield in charge Avondale won the
FAI Intermediate Cup in 2005–06 and 2006–07 and two
Munster Premier Division titles in 2008–09 and 2009–10. With Caulfield in charge, Cork City have finished as runners-up in the
League of Ireland Premier Division in
2014,
2015 and
2016. They were also runners-up in the
2015 FAI Cup. In 2016 Caulfield guided Cork City to victory in both the
President's Cup and the
FAI Cup. In the
2016 FAI Cup Final, City won when
Sean Maguire scored a last minute extra time goal against
Dundalk. 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. Genk. The victory over Linfield ensured that Caulfield was the first American-born manager to progress in a two-legged tie in European competition. When Caulfield managed Cork City to the
2017 League of Ireland Premier Division title a year later, he became the first American-born manager to win a top-tier league in Europe. He followed up this success by coaching his team to victory in the
2017 FAI Cup, thus completing the double. 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. On 28 November 2025, Caulfield signed a new two-year-contract with the club. ==Managerial statistics==