| Queens Park Rangers FC v Birmingham City FC 27/10/1999 | £5.00 | |
| Arsenal FC v AC Fiorentina 27/10/1999 | £4.00 | |
| Tottenham Hotspur FC v Kaiserslautern 28/10/1999 | £5.00 | |
| Luton Town FC v Kingstonian FC 30/10/1999 | £6.00 | |
| Peterborough United FC v Brighton & Hove Albion FC 30/10/1999 | £5.50 | |
| Tamworth v Bury FC 30/10/1999 | £6.50 | |
| Derby County FC v Chelsea FC 30/10/1999 | £6.50 | |
| Arsenal FC v Newcastle United FC 30/10/1999 | £2.50 | |
| Arsenal FC v Newcastle United FC 30/10/1999 | £3.50 | |
| Sunderland FC v Tottenham Hotspur FC 31/10/1999 | £6.50 | |
| Southend United FC v Brighton & Hove Albion FC 02/11/1999 | £7.00 | |
| Bristol Rovers FC v Bury FC 02/11/1999 | £6.00 |