1998–99 Chester City F.C. season

The 1998–99 season was the 61st season of competitive association football in the Football League played by Chester City, an English club based in Chester, Cheshire.

Also, it was the fourth season spent in the Third Division, after the relegation from the Second Division in 1995. Alongside competing in the Football League the club also participated in the FA Cup, the Football League Cup and the Football League Trophy.