2005–06 Chester City F.C. season

The 2005–06 season was the 64th season of competitive association football in the Football League played by Chester City, an English club based in Chester, Cheshire.

Also, it was the second season spent in the Football League Two, after the promotion from the Football Conference in 2004. Alongside competing in the Football League the club also participated in the FA Cup, the Football League Cup and the Football League Trophy.