| 1. Journée | 07.08.1999 | Coventry City | - | Southampton FC | 0:1 | ||||
| 2. Journée | 11.08.1999 | Leicester City | - | Coventry City | 1:0 | ||||
| 4. Journée | 21.08.1999 | Coventry City | - | Derby County | 2:0 | ||||
| 5. Journée | 25.08.1999 | Coventry City | - | Manchester United | 1:2 | ||||
| 6. Journée | 29.08.1999 | Sunderland AFC | - | Coventry City | 1:1 | ||||
| 7. Journée | 11.09.1999 | Coventry City | - | Leeds United | 3:4 | ||||
| 8. Journée | 19.09.1999 | Tottenham Hotspur | - | Coventry City | 3:2 | ||||
| 9. Journée | 25.09.1999 | Coventry City | - | West Ham United | 1:0 |  |
|||
| 10. Journée | 02.10.1999 | Everton FC | - | Coventry City | 1:1 | |
|||
| 11. Journée | 16.10.1999 | Coventry City | - | Newcastle United | 4:1 | |
Angleterre