| 02 Sep 08 | r00        | BirminghamBirmingham | 2 - 0 | BoltonBolton |
| 05 Sep 08 | r00        | BarnsleyBarnsley | 0 - 1 | BoltonBolton |
| 12 Sep 08 | r00        | BoltonBolton | 4 - 0 | GainsboroughGainsborough |
| 14 Sep 08 | r00        | BoltonBolton | 1 - 0 | HullHull |
| 15 Sep 08 | r00        | BoltonBolton | 1 - 1 | West BromWest Brom |
| 19 Sep 08 | r00        | TottenhamTottenham | 2 - 1 | BoltonBolton |
| 26 Sep 08 | r00        | BoltonBolton | 2 - 0 | GrimsbyGrimsby |
| 03 Oct 08 | r00        | HullHull | 2 - 0 | BoltonBolton |
| 10 Oct 08 | r00        | BoltonBolton | 0 - 0 | FulhamFulham |
| 17 Oct 08 | r00        | DerbyDerby | 1 - 0 | BoltonBolton |
| 24 Oct 08 | r00        | BoltonBolton | 2 - 1 | BurnleyBurnley |
| 31 Oct 08 | r00        | BlackpoolBlackpool | 1 - 2 | BoltonBolton |
| 07 Nov 08 | r00        | BoltonBolton | 0 - 1 | Bradford Park AvenueBradford Park |
| 14 Nov 08 | r00        | ChesterfieldChesterfield | 0 - 2 | BoltonBolton |
| 21 Nov 08 | r00        | BoltonBolton | 1 - 1 | WolvesWolves |
| 28 Nov 08 | r00        | Glossop North End AFCGlossop North | 0 - 2 | BoltonBolton |
| 05 Dec 08 | r00        | BoltonBolton | 3 - 0 | OldhamOldham |
| 12 Dec 08 | r00        | StockportStockport | 1 - 0 | BoltonBolton |
| 19 Dec 08 | r00        | BoltonBolton | 2 - 0 | Leyton OrientLeyton Orient |
| 25 Dec 08 | r00        | BoltonBolton | 2 - 0 | Leeds City FCLeeds City FC |
| 26 Dec 08 | r00        | Leeds City FCLeeds City FC | 1 - 2 | BoltonBolton |
| 01 Jan 09 | r00        | BoltonBolton | 2 - 1 | BirminghamBirmingham |
| 02 Jan 09 | r00        | BoltonBolton | 3 - 0 | BarnsleyBarnsley |
| 09 Jan 09 | r00        | GainsboroughGainsborough | 2 - 1 | BoltonBolton |
| 23 Jan 09 | r00        | BoltonBolton | 0 - 1 | TottenhamTottenham |
| 30 Jan 09 | r00        | GrimsbyGrimsby | 1 - 0 | BoltonBolton |
| 13 Feb 09 | r00        | FulhamFulham | 1 - 2 | BoltonBolton |
| 20 Feb 09 | r00        | BoltonBolton | 4 - 0 | ChesterfieldChesterfield |
| 27 Feb 09 | r00        | BurnleyBurnley | 1 - 2 | BoltonBolton |
| 06 Mar 09 | r00        | BoltonBolton | 3 - 1 | BlackpoolBlackpool |
| 13 Mar 09 | r00        | Bradford Park AvenueBradford Park | 1 - 2 | BoltonBolton |
| 27 Mar 09 | r00        | WolvesWolves | 1 - 2 | BoltonBolton |
| 03 Apr 09 | r00        | BoltonBolton | 2 - 0 | Glossop North End AFCGlossop North |
| 10 Apr 09 | r00        | OldhamOldham | 1 - 1 | BoltonBolton |
| 12 Apr 09 | r00        | West BromWest Brom | 2 - 0 | BoltonBolton |
| 17 Apr 09 | r00        | BoltonBolton | 4 - 1 | StockportStockport |
| 24 Apr 09 | r00        | Leyton OrientLeyton Orient | 0 - 2 | BoltonBolton |
| 30 Apr 09 | r00        | BoltonBolton | 1 - 0 | DerbyDerby |