| Arsenal FC v Middlesbrough FC 20/11/1999 | £2.50 | |
| Arsenal FC v Middlesbrough FC 20/11/1999 | £4.00 | |
| Arsenal FC v Nantes Altantique 25/11/1999 | £4.00 | |
| Arsenal FC v Derby County FC 28/11/1999 | £3.50 | |
| Middlesbrough FC v Arsenal FC 30/11/1999 | View match | |
| Leicester City FC v Arsenal FC 04/12/1999 | View match | |
| Nantes Altantique v Arsenal FC 09/12/1999 | View match | |
| Arsenal FC v Blackpool FC 13/12/1999 | £2.00 | |
| Arsenal FC v Blackpool FC 13/12/1999 | £4.50 | |
| Arsenal FC v Wimbledon 18/12/1999 | £5.00 | |
| Coventry City FC v Arsenal FC 26/12/1999 | View match | |
| Arsenal FC v Leeds United FC 28/12/1999 | £5.00 |