| Southampton FC v Coventry City FC 04/12/1999 | £3.50 | |
| Southampton FC v Coventry City FC 04/12/1999 | £4.50 | |
| Liverpool FC v Sheffield Wednesday FC 05/12/1999 | £5.50 | |
| Tottenham Hotspur FC v West Ham United FC 06/12/1999 | £4.50 | |
| Tottenham Hotspur FC v West Ham United FC 06/12/1999 | £3.50 | |
| Crystal Palace FC v Ipswich Town FC 07/12/1999 | £2.50 | |
| Manchester City FC v Stockport County FC 07/12/1999 | £7.00 | |
| Lazio SS v Chelsea FC 07/12/1999 | £10.00 | |
| Mansfield Town FC v Bury FC 07/12/1999 | £5.50 | |
| Manchester United FC v Valencia CF 08/12/1999 | £2.50 | |
| Brighton & Hove Albion FC v Rochdale FC 10/12/1999 | £6.00 | |
| Charlton Athletic FC v Swindon Town FC 11/12/1999 | £4.50 |