 Kirkland made his debut for Coventry in the League Cup in a 3–1 victory over Tranmere Rovers at Highfield Road on 22 September 1999.Manager Gordon Strachan began selecting him in Premier League matches ahead of Swedish international Magnus Hedman despite saying Kirkland was "big Bambi who couldn't kick the ball out of the penalty box".His performances were rewarded at the end of the 2000–01 season when he made his debut for the England under-21s, and was voted Coventry's Players' Player of the Year by his teammates.