| Southampton FC v Derby County FC 04/10/1999 | £2.50 | |
| Queens Park Rangers FC v Tranmere Rovers FC 09/10/1999 | £5.00 | |
| Bury FC v Notts County FC 09/10/1999 | £6.00 | |
| Carlisle United FC v Brighton & Hove Albion FC 09/10/1999 | £6.50 | |
| Arsenal FC v Preston North End FC 12/10/1999 | £4.50 | |
| Southampton FC v Liverpool FC 13/10/1999 | £6.50 | |
| Chelsea FC v Huddersfield Town FC 13/10/1999 | £4.50 | |
| Chelsea FC v Huddersfield Town FC 13/10/1999 | £3.50 | |
| Tottenham Hotspur FC v Crewe Alexandra FC 13/10/1999 | £3.50 | |
| Tottenham Hotspur FC v Crewe Alexandra FC 13/10/1999 | £5.00 | |
| Blackpool FC v Bury FC 16/10/1999 | £5.00 | |
| Derby County FC v Tottenham Hotspur FC 16/10/1999 | £4.00 |