| Middlesbrough FC v Arsenal FC 24/04/1999 | View match | |
| Arsenal FC v Derby County FC 02/05/1999 | £2.00 | |
| Tottenham Hotspur FC v Arsenal FC 05/05/1999 | £4.50 | |
| Tottenham Hotspur FC v Arsenal FC 05/05/1999 | £3.00 | |
| Leeds United FC v Arsenal FC 11/05/1999 | View match | |
| Arsenal FC v Aston Villa FC 16/05/1999 | £2.50 | |
| Arsenal FC v Manchester United FC 01/08/1999 | £6.00 | |
| Arsenal FC v Leicester City FC 07/08/1999 | £1.50 | |
| Arsenal FC v Leicester City FC 07/08/1999 | £4.00 | |
| Derby County FC v Arsenal FC 10/08/1999 | £3.50 | |
| Sunderland FC v Arsenal FC 14/08/1999 | View match | |
| Arsenal FC v Manchester United FC 22/08/1999 | £3.00 |