| Southampton FC v West Ham United FC 06/03/1999 | £2.00 | |
| Southampton FC v Sheffield Wednesday FC 20/03/1999 | £2.50 | |
| Southampton FC v Sheffield Wednesday FC 20/03/1999 | £3.50 | |
| Southampton FC v Arsenal FC 03/04/1999 | £3.00 | |
| Coventry City FC v Southampton FC 05/04/1999 | £5.00 | |
| Aston Villa FC v Southampton FC 10/04/1999 | £4.00 | |
| Southampton FC v Blackburn Rovers FC 17/04/1999 | £2.00 | |
| Southampton FC v Blackburn Rovers FC 17/04/1999 | £2.50 | |
| 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 |