| 02 Sep 99 | r00        | Glossop North End AFCGlossop North | 2 - 0 | BurnleyBurnley |
| 04 Sep 99 | r00        | Aston VillaAston Villa | 9 - 0 | Glossop North End AFCGlossop North |
| 09 Sep 99 | r00        | PrestonPreston | 1 - 0 | Glossop North End AFCGlossop North |
| 16 Sep 99 | r00        | Glossop North End AFCGlossop North | 3 - 0 | Nottingham F.Nottingham F. |
| 23 Sep 99 | r00        | WolvesWolves | 4 - 0 | Glossop North End AFCGlossop North |
| 30 Sep 99 | r00        | StokeStoke | 1 - 0 | Glossop North End AFCGlossop North |
| 07 Oct 99 | r00        | Glossop North End AFCGlossop North | 0 - 2 | SunderlandSunderland |
| 14 Oct 99 | r00        | West BromWest Brom | 3 - 3 | Glossop North End AFCGlossop North |
| 21 Oct 99 | r00        | Glossop North End AFCGlossop North | 1 - 1 | EvertonEverton |
| 11 Nov 99 | r00        | BuryBury | 2 - 1 | Glossop North End AFCGlossop North |
| 18 Nov 99 | r00        | Glossop North End AFCGlossop North | 0 - 0 | Notts CountyNotts County |
| 25 Nov 99 | r00        | Manchester CityManchester Ci | 4 - 1 | Glossop North End AFCGlossop North |
| 02 Dec 99 | r00        | Glossop North End AFCGlossop North | 2 - 2 | Sheffield UnitedSheffield Uni |
| 16 Dec 99 | r00        | Glossop North End AFCGlossop North | 1 - 0 | Aston VillaAston Villa |
| 23 Dec 99 | r00        | LiverpoolLiverpool | 5 - 2 | Glossop North End AFCGlossop North |
| 26 Dec 99 | r00        | DerbyDerby | 4 - 1 | Glossop North End AFCGlossop North |
| 29 Dec 99 | r00        | BurnleyBurnley | 3 - 1 | Glossop North End AFCGlossop North |
| 06 Jan 00 | r00        | Glossop North End AFCGlossop North | 0 - 2 | PrestonPreston |
| 13 Jan 00 | r00        | Nottingham F.Nottingham F. | 5 - 0 | Glossop North End AFCGlossop North |
| 20 Jan 00 | r00        | Glossop North End AFCGlossop North | 2 - 3 | WolvesWolves |
| 03 Feb 00 | r00        | Glossop North End AFCGlossop North | 1 - 2 | StokeStoke |
| 24 Feb 00 | r00        | SunderlandSunderland | 0 - 0 | Glossop North End AFCGlossop North |
| 27 Feb 00 | r00        | Glossop North End AFCGlossop North | 4 - 2 | BlackburnBlackburn |
| 03 Mar 00 | r00        | BlackburnBlackburn | 2 - 2 | Glossop North End AFCGlossop North |
| 14 Mar 00 | r00        | NewcastleNewcastle | 1 - 0 | Glossop North End AFCGlossop North |
| 17 Mar 00 | r00        | Glossop North End AFCGlossop North | 0 - 0 | BuryBury |
| 24 Mar 00 | r00        | Notts CountyNotts County | 0 - 0 | Glossop North End AFCGlossop North |
| 31 Mar 00 | r00        | Glossop North End AFCGlossop North | 0 - 2 | Manchester CityManchester Ci |
| 07 Apr 00 | r00        | Sheffield UnitedSheffield Uni | 4 - 0 | Glossop North End AFCGlossop North |
| 13 Apr 00 | r00        | Glossop North End AFCGlossop North | 1 - 3 | DerbyDerby |
| 14 Apr 00 | r00        | Glossop North End AFCGlossop North | 0 - 0 | NewcastleNewcastle |
| 16 Apr 00 | r00        | EvertonEverton | 4 - 1 | Glossop North End AFCGlossop North |
| 24 Apr 00 | r00        | Glossop North End AFCGlossop North | 1 - 1 | West BromWest Brom |
| 28 Apr 00 | r00        | Glossop North End AFCGlossop North | 1 - 2 | LiverpoolLiverpool |