| Southampton FC v Everton FC 16/05/1999 | £4.00 | |
| Coventry City FC v Southampton FC 07/08/1999 | £3.50 | |
| Southampton FC v Leeds United FC 11/08/1999 | £3.50 | |
| Southampton FC v Leeds United FC 11/08/1999 | £3.50 | |
| Southampton FC v Newcastle United FC 15/08/1999 | £3.00 | |
| Southampton FC v Newcastle United FC 15/08/1999 | £3.50 | |
| Everton FC v Southampton FC 21/08/1999 | View match | |
| Southampton FC v Sheffield Wednesday FC 28/08/1999 | £3.50 | |
| Middlesbrough FC v Southampton FC 11/09/1999 | £6.50 | |
| Manchester City FC v Southampton FC 15/09/1999 | £12.50 | |
| Southampton FC v Arsenal FC 18/09/1999 | £3.50 | |
| Southampton FC v Manchester City FC 21/09/1999 | View match |