John Caulfield’s name is famous in Cork for what he achieved with City in League of Ireland football both as a player and as a manager.

As a player he enjoyed a successful career, spending most of his playing days with Cork City, where he holds the record for most appearances made and he’s also the club's joint-top goalscorer along with Pat Morley.

The former striker picked up plenty of silverware as a player also, winning the Premier Division title, an FAI Cup, three League Cups, and 11 Munster Senior Cups.

During his tenure at Turners Cross, Cork City were consistently challenging for domestic honours and they finished runners-up in the Premier Division on four occasions, whilst also reaching the FAI Cup final four times in a row, meeting Dundalk each time between 2015 and 2018. They would lift the cup in 2016 before winning a historic league and cup double in 2017.

Caulfield also led the Leesiders back into Europe, managing them in both the UEFA Champions League and Europa League, enjoying memorable nights in the latter back in 2016 as they defeated Linfield and Swedish side BK Hacken in the Europa League before they were eventually eliminated by KRC Gent.

He departed the Rebel Army in 2019 following a tough start to the season and is now managing Galway United in the first division.