| Manchester City FC v Southampton FC 15/09/1999 | £12.50 | |
| Southampton FC v Arsenal FC 18/09/1999 | £3.50 | |
| Southampton FC v Derby County FC 04/10/1999 | £3.50 | |
| Southampton FC v Derby County FC 04/10/1999 | £2.50 | |
| Southampton FC v Liverpool FC 13/10/1999 | £6.50 | |
| Southampton FC v Liverpool FC 23/10/1999 | £4.50 | |
| Southampton FC v Tottenham Hotspur FC 20/11/1999 | £3.50 | |
| Southampton FC v Tottenham Hotspur FC 20/11/1999 | £2.00 | |
| 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 | £3.50 |