 |
 |
| League Two | 13.01.2009 | Chester City | - | Luton Town | 2:2 | 1.652 |
| League Two | 17.01.2009 | Chester City | - | Chesterfield FC | 1:3 | 1.806 |
| League Two | 31.01.2009 | Chester City | - | Gillingham FC | 0:1 | 1.541 |
| League Two | 03.02.2009 | Chester City | - | Rochdale AFC | 0:2 | 1.357 |
| League Two | 21.02.2009 | Chester City | - | Exeter City | 0:0 | 1.640 |
| League Two | 28.02.2009 | Chester City | - | Dagenham & Redbridge | 2:2 | 1.416 |
| League Two | 10.03.2009 | Chester City | - | Rotherham United | 1:5 | 1.235 |
| League Two | 14.03.2009 | Chester City | - | Grimsby Town | 1:1 | 2.836 |
| League Two | 28.03.2009 | Chester City | - | Bradford City | 0:0 | 2.735 |
| League Two | 11.04.2009 | Chester City | - | Macclesfield Town | 0:2 | 2.248 |
| League Two | 18.04.2009 | Chester City | - | AFC Bournemouth | 0:2 | 3.349 |
| League Two | 02.05.2009 | Chester City | - | Darlington FC | 1:2 | 1.945 |
Angleterre