Darlington's fixtures and results for the 2008/09 season can be seen below. Home games are highlighted whilst Darlington's score is always first. Match reports can be read by simply clicking on the link.
| Date | Opponent | V | KO | Comp | Score | Att |
| 9 Aug | Exeter City | H | 3:00 PM | League Two | 1-1 | 3,559 |
| 12 Aug | Walsall | A | 7:45 PM | League Cup | 2-1 | 2,702 |
| 16 Aug | Notts County | A | 3:00 PM | League Two | 0-0 | 4,352 |
| 23 Aug | Gillingham | H | 3:00 PM | League Two | 1-2 | 2,831 |
| 26 Aug | Watford | A | 7:45 PM | League Cup | 1-2 | 5,236 |
| 30 Aug | Macclesfield Town | A | 3:00 PM | League Two | 6-0 | 1,554 |
| 6 Sep | Aldershot | A | 3:00 PM | League Two | 1-2 | 3,460 |
| 13 Sep | Port Vale | H | 3:00 PM | League Two | 2-1 | 3,040 |
| 20 Sep | Accrington Stanley | H | 3:00 PM | League Two | 3-0 | 2,814 |
| 27 Sep | Bournemouth | A | 3:00 PM | League Two | 1-3 | 4,124 |
| 4 Oct | Shrewsbury Town | H | 3:00 PM | League Two | 1-1 | 2,899 |
| 7 Oct | Huddersfield Town | H | 7:45 PM | JPT | 1-0 | 1,791 |
| 11 Oct | Luton Town | A | 3:00 PM | League Two | 2-1 | 5,560 |
| 18 Oct | Wycombe Wanderers | A | 3:00 PM | League Two | 1-1 | 5,345 |
| 20 Oct | Bradford City | H | 7:45 PM | League Two | 2-1 | 3,034 |
| 25 Oct | Dagenham & Redbridge | H | 3:00 PM | League Two | 3-0 | 3,070 |
| 28 Oct | Rotherham | A | 7:45 PM | League Two | 1-0 | 3,322 |
| 1 Nov | Grimsby Town | A | 3:00 PM | League Two | 2-1 | 3,509 |
| 4 Nov | Bury | H | 7:45 PM | JPT | 1-0 | 1,651 |
| 8 Nov | Droylsden | H | 3:00 PM | FA Cup | 0-0 | 2,479 |
| 15 Nov | Lincoln City | H | 3:00 PM | League Two | 2-0 | 3,534 |
| 18 Nov | Droylsden | A | 7:45 PM | FA Cup | 0-1 | 1,672 |
| 22 Nov | Brentford | A | 3:00 PM | League Two | ||
| 25 Nov | Chester City | H | 7:45 PM | League Two |