He picked up the Player of the Season award for 1999–2000, and played for Birmingham in the 2001 Football League Cup Final loss to Liverpool, missing one of the spot kicks in the shootout. As Birmingham continued to improve in the First Division, and eventually earned promotion into the Premiership, Grainger's playing time became limited. He failed to appear for Birmingham due to injury during the first half of the 2003–04 season, and in February he was loaned to Coventry City, for whom he made seven league appearances. On 18 March 2004, he was recalled to Birmingham's team due to an injury crisis, and got on the scoresheet in a 2–1 defeat to Manchester United, but was himself injured and failed to appear in any matches for the rest of the season.