| Southampton FC v Newcastle United FC 20/02/1999 | £2.50 | |
| Manchester United FC v Southampton FC 27/02/1999 | £9.00 | |
| Manchester United FC v Southampton FC 27/02/1999 | £6.50 | |
| Tottenham Hotspur FC v Southampton FC 02/03/1999 | £2.00 | |
| Tottenham Hotspur FC v Southampton FC 02/03/1999 | £4.50 | |
| Southampton FC v West Ham United FC 06/03/1999 | £2.00 | |
| Middlesbrough FC v Southampton FC 14/03/1999 | View match | |
| Southampton FC v Sheffield Wednesday FC 20/03/1999 | £3.50 | |
| Southampton FC v Sheffield Wednesday FC 20/03/1999 | £2.50 | |
| Southampton FC v Arsenal FC 03/04/1999 | £3.00 | |
| Coventry City FC v Southampton FC 05/04/1999 | View match | |
| Aston Villa FC v Southampton FC 10/04/1999 | £4.00 |