James Bailey is another graduate of the famous Crewe Alexandra Academy having been with the club since he was a young boy. Bailey worked his way through the ranks, signing professional in 2007. The following December he made his professional debut against Doncaster Rovers as a late substitute.

He really made his impact on the side though, in the pre-season ahead of the 2008/09 campaign forcing his way into the first team plans. 'Bails' as he was known at the Alex, made his full debut against Brighton on the opening day of the season in an influential Alex midfield. Injury kept hampering his progress, but he came out stronger every time and with some continuing impressive displays the scouts began to flock to the Alexandra Stadium.

Macclesfield born, Bailey has a mature way of playing and during his time at Crewe was described as one of the best passers of the ball in the lower leagues. His passing ability caught the eye of Nigel Clough at Derby County, and in the summer of 2010, after three years as a professional with Crewe Alexandra, Bailey went for pastures new in the Championship with the Rams.

Bailey would make 38 appearances for the Rams in his first year at Pride Park, and would score his one and only goal for County in a 2-2 draw with the eventual winners of the Championship QPR. Bailey was also voted the clubs Young Player of the Season.