1999–2000 Chester City F.C. season

The 1999–2000 season was the 62nd season of competitive association football in the Football League played by Chester City, an English club based in Chester, Cheshire.

Also, it was the fifth 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.