| Southampton FC v Blackburn Rovers FC 17/04/1999 | £2.50 | |
| Southampton FC v Blackburn Rovers FC 17/04/1999 | £2.00 | |
| Southampton FC v Leicester City FC 01/05/1999 | £2.00 | |
| Southampton FC v Leicester City FC 01/05/1999 | £2.50 | |
| 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 | £3.50 | |
| Southampton FC v Newcastle United FC 15/08/1999 | £3.00 | |
| Southampton FC v Sheffield Wednesday FC 28/08/1999 | £3.50 | |
| Middlesbrough FC v Southampton FC 11/09/1999 | £6.50 |