| Southampton FC v Chelsea FC 26/12/1999 | £2.50 | |
| Southampton FC v Chelsea FC 26/12/1999 | £3.00 | |
| Southampton FC v Chelsea FC 26/12/1999 | £3.50 | |
| Southampton FC v Chelsea FC 26/12/1999 | £3.50 | |
| Southampton FC v Chelsea FC 26/12/1999 | £3.00 | |
| Watford FC v Southampton FC 28/12/1999 | £6.50 | |
| Southampton FC v Bradford City FC 03/01/2000 | £4.00 | |
| Southampton FC v Bradford City FC 03/01/2000 | £2.00 | |
| Aston Villa FC v Southampton FC 08/01/2000 | View match | |
| Newcastle United FC v Southampton FC 16/01/2000 | View match | |
| Southampton FC v Everton FC 22/01/2000 | View match | |
| Southampton FC v West Ham United FC 05/02/2000 | £4.50 |