Holland's managerial experience at club level includes stints in charge of Clonakilty and the Carbery divisional team. He spent a number of seasons as a selector with the Cork senior football team and was part of three Munster Championship-winning management teams. His tenure as a selector also saw Cork lose the 1993 All-Ireland final to Derry. After a spell as a selector with the under-21 side, Holland was appointed manager of the Cork minor football team and guided the team to the All-Ireland Minor Championship title in 2000.[2] He was appointed manager of the Cork senior team in November 2007 while the entire team of players were on strike as a protest about the process for picking the selectors.[3] The players refused to play under Holland as he was appointed during the strike.[4] The strike lasted until 18 February 2008 when he resigned as manager as one of the conditions for resolving the strike.[5]