Gameplan
| Date | Round | Match | Match | Res. | Attendance | |
|---|---|---|---|---|---|---|
| 13.01.2009 |  | Matchday 24 | Chester City - Luton Town | Che - LUT | 2:2 | 1.652 |
| 17.01.2009 | | Matchday 26 | Chester City - Chesterfield FC | Che - CHF | 1:3 | 1.806 |
| 31.01.2009 | | Matchday 29 | Chester City - Gillingham FC | Che - GIL | 0:1 | 1.541 |
| 03.02.2009 | | Matchday 30 | Chester City - Rochdale AFC | Che - ROC | 0:2 | 1.357 |
| 21.02.2009 | | Matchday 33 | Chester City - Exeter City | Che - EXE | 0:0 | 1.640 |
| 28.02.2009 | | Matchday 34 | Chester City - Dagenham & Redb | Che - D&R | 2:2 | 1.416 |
| 10.03.2009 | | Matchday 37 | Chester City - Rotherham Utd | Che - ROT | 1:5 | 1.235 |
| 14.03.2009 | | Matchday 38 | Chester City - Grimsby Town | Che - GRI | 1:1 | 2.836 |
| 28.03.2009 | | Matchday 40 | Chester City - Bradford | Che - BRA | 0:0 | 2.735 |
| 11.04.2009 | | Matchday 42 | Chester City - Macclesfield FC | Che - MAC | 0:2 | 2.248 |
| 18.04.2009 | | Matchday 44 | Chester City - Bournemouth | Che - BOU | 0:2 | 3.349 |
| 02.05.2009 | | Matchday 46 | Chester City - Darlington FC | Che - DAR | 1:2 | 1.945 |