29 April 2001 against Rangers at Ibrox Stadium, in a 3–0 win for Celtic. He spent the next few years trying to break into the first team, spending most of his time as a substitute. Despite not playing regularly, Maloney acquired a reputation for being a free kick specialist. Maloney did appear several times for Celtic during their run to the UEFA Cup Final in 2003, and scored in a 3–1 win over VfB Stuttgart at Parkhead in the Round of 16. In February 2004, Maloney picked up a cruciate ligament injury. He returned from the injury late in season 2004–05, starting only one game in that season. Maloney hit top form for Celtic in the 2005–06 season, after being moved from a striking position to the left of midfield by manager Gordon Strachan. His displays received praise from players, fans and the media throughout the year, and in recognition of his excellent season he was awarded both the SPFA Player of the Year and Young Player of the Year awards, the first time a player has won both plaudits in the same season. He also won Celtic Fans' Player of the Year, and Players Player of the Year in a season which saw him score 16 goals and contribute 28 assists from midfield. With his contract expiring at the end of the 2006–07 season, Celtic moved to offer Maloney a new deal. However, contract negotiations continued for months, constantly breaking down due to differences between the two parties. Chief Executive Peter Lawwell asserted that Celtic "cannot keep players at any cost" while Maloney warned that "In situations like this one, both parties have to be completely happy with the outcome." He also promised that the prolonged contract talks would not affect his football and that he hoped he would not have to consider leaving the club in the future. Maloney would have been able to leave Celtic for free in the summer of 2007, by signing a pre-contract agreement with another club. No new contract was agreed with Celtic, and they subsequently agreed a £1 million transfer to Aston Villa. In his first tenure, Maloney made a total of 139 appearances for the Hoops in all competitions, scoring 37 times. Aston Villa Just before the transfer window closed on 31 January 2007, Maloney signed a pre-contract agreement with Aston Villa. Villa manager Martin O'Neill, who managed him at Celtic,