| Blackpool FC v Bury FC 16/10/1999 | View match | |
| Blackpool FC v Oldham Athletic FC 19/10/1999 | View match | |
| Wycombe Wanderers FC v Blackpool FC 23/10/1999 | View match | |
| Blackpool FC v Stoke City FC 30/10/1999 | View match | |
| Cardiff City FC v Blackpool FC 02/11/1999 | View match | |
| Blackpool FC v Wigan Athletic FC 06/11/1999 | View match | |
| Burnley FC v Blackpool FC 14/11/1999 | View match | |
| Blackpool FC v Hendon FC 20/11/1999 | View match | |
| Blackpool FC v Millwall FC 23/11/1999 | View match | |
| Blackpool FC v Cambridge United FC 27/11/1999 | View match | |
| Wrexham FC v Blackpool FC 04/12/1999 | View match | |
| Arsenal FC v Blackpool FC 13/12/1999 | £4.50 |