| Southampton FC v Tottenham Hotspur FC 20/11/1999 | £3.50 | |
| Leeds United FC v Southampton FC 28/11/1999 | £3.00 | |
| Southampton FC v Coventry City FC 04/12/1999 | £3.50 | |
| Southampton FC v Coventry City FC 04/12/1999 | £4.50 | |
| Southampton FC v Coventry City FC 04/12/1999 | £3.50 | |
| Sunderland FC v Southampton FC 18/12/1999 | £4.00 | |
| Southampton FC v Chelsea FC 26/12/1999 | £3.50 | |
| Southampton FC v Chelsea FC 26/12/1999 | £2.50 | |
| Southampton FC v Chelsea FC 26/12/1999 | £3.50 | |
| Southampton FC v Chelsea FC 26/12/1999 | £3.00 | |
| Southampton FC v Chelsea FC 26/12/1999 | £3.00 | |
| Watford FC v Southampton FC 28/12/1999 | £6.50 |