They made it to the 1999 FAI Cup Final but lost to Bray Wanderers after a number of replays, leaving themselves with nothing to show (bar the Irish News Cup) for what is considered to be one of their most impressive seasons. After a very poor start to the 1999–00 season, and with the team having won one point from a possible 21, McGeever resigned as manager. The club appointed Gavin Dykes as manager and, though he managed to retain the club's Premier Division status, they were forced to go public company due to financial difficulties and debts amounting to £280,000. The following season, and after an abysmal run of results, Dykes resigned. Fan-favourite Jonathan Speak took his place as new financial structures were put into place and a newly appointed fund-raising committee established along with numerous supporter clubs around the country. However, after a run of 14 games undefeated and a late-season fightback, Finn Harps were ultimately relegated to the First Division on the last day of the season. This ended a five-year run in the top flight. The yo-yo years Speak's first full season in charge saw the club finish second to Drogheda United in the First Division, thus securing them a play-off place for promotion. Longford Town beat them on penalties. The following season saw the club finish third and lose at the play-off semi-final stage to Galway United. Speak managed to hold most of the squad together, despite their top-scorer Kevin McHugh (who formed a successful forward partnership with English striker Damien Whitehead) attracting the interest of several Premier Division clubs. Considered bookmaker's favourites to lift the 2003 title and win promotion, Finn Harps began well but fell to fourth position after having gone without a win for a month by mid-September. This poor run included a home-loss to the neighbouring northwest club Sligo Rovers and a home-draw against league leaders Dublin City, the latter game billed as a must-win match. Despite losing only two games for the entire season, the nine draws cost Speak his job. Speak's assistant, Sean McGowan, took temporary charge until a suitable placement was found and steadied the club with two wins from two. Approaching the final third of the season, the club appointed Noel King as manager. They were rejuvenated and stormed back to the top of the First Division table with a club record-equalling six wins on the trot.