| Southampton FC v Middlesbrough FC 04/03/2000 | £3.50 | |
| Tottenham Hotspur FC v Southampton FC 11/03/2000 | £4.50 | |
| Tottenham Hotspur FC v Southampton FC 11/03/2000 | £3.00 | |
| Southampton FC v Aston Villa FC 18/03/2000 | £3.50 | |
| Chelsea FC v Southampton FC 25/03/2000 | £3.00 | |
| Southampton FC v Sunderland FC 01/04/2000 | £3.50 | |
| Southampton FC v Watford FC 15/04/2000 | £3.50 | |
| Southampton FC v Manchester United FC 22/04/2000 | £6.00 | |
| Southampton FC v Leicester City FC 29/04/2000 | £3.00 | |
| Southampton FC v Leicester City FC 29/04/2000 | £3.50 | |
| Liverpool FC v Southampton FC 07/05/2000 | £2.50 | |
| Southampton FC v Wimbledon 14/05/2000 | £3.50 |