| Arsenal FC v Wimbledon 19/04/1999 | £3.50 | |
| 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 | |
| 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 | £4.00 | |
| Arsenal FC v Leicester City FC 07/08/1999 | £1.50 | |
| Derby County FC v Arsenal FC 10/08/1999 | £3.50 | |
| Arsenal FC v Manchester United FC 22/08/1999 | £6.00 | |
| Arsenal FC v Manchester United FC 22/08/1999 | £3.00 | |
| Arsenal FC v Bradford City FC 25/08/1999 | £2.00 |