 He made a personal-best 52 appearances during the 2008–09 season, scoring two goals and helping Millwall to a place at Wembley Stadium for the 2009 League One play-off Final versus Scunthorpe United.Goals from Gary Alexander put the Lions 2–1 ahead, but the season ended in heartbreak for Craig after second half strikes from Matt Sparrow and Martyn Woolford sent Scunthorpe to the Championship.Craig was in and out of the team during the 2009–10 season and could not hold down a regular place until December 2009.