Cup. 2006 saw further upgrade work begin at Turners Cross and City met Apollon Limassol and Red Star Belgrade in the UEFA Champions League. The club lost to Drogheda United in the Setanta Cup Final, finished 4th in the league, and secured a place in the Intertoto and Setanta Cup. At the start of the 2007 season, two new signings were deemed ineligible for play. This mirrored an inconsistent season start, with elimination from the Setanta Cup, a home win against St. Pat's and a record-equaling 4–1 defeat to Sligo Rovers. In August 2007, Roy O'Donovan left for Sunderland for a record LOI fee of €500,000. 2007 also saw the club's ownership change hands: from chairman Brian Lennox to venture capital firm "Arkaga". Despite an FAI Cup win, manager Damien Richardson's future at the club was in doubt, and – after some acrimony – he and the club parted ways. In January 2008, former Longford Town boss Alan Mathews became manager, and the club signed several players – including taking advantage of FIFA's changes to the "3 club" rule by re-signing George O'Callaghan from Ipswich Town. However O'Callaghan was later dropped and released. City were knocked out of the first qualifying round in European competition by FC Haka. While David Mooney retained the league's top scorer spot, City failed to take points from Bohemians or St. Pats and finished fifth in the league. The club did however gain some silverware, beating Glentoran in the Setanta Sports Cup final. Off the pitch the club suffered a considerable threat when, in August 2008, after investment difficulties with venture capital firm Arkaga, the club entered into examinership. With debts of up to €800,000, cost-cutting measures were implemented. Under related rules, the club was docked 10 points in the league. In October 2008 the High Court ruled in favour of Tom Coughlan's bid to take over the club, and ended the examinership. Paul Doolin replaced Mathews as manager for the 2009 season, and the side gained a number of positive results early in 2009 – including defeating Roy Keane's touring Ipswich Town 2–0. Despite these on pitch results however, the club's future was left in considerable doubt following a High Court decision on outstanding Revenue receipts. A "winding up" order was issued when no agreement could be reached on tax payments. The club were given several extensions to pay or to appeal, and the