| Arsenal FC v Aston Villa FC 11/09/1999 | £2.00 | |
| Arsenal FC v Aston Villa FC 11/09/1999 | £3.50 | |
| Arsenal FC v Aston Villa FC 11/09/1999 | £2.50 | |
| Arsenal FC v Aston Villa FC 11/09/1999 | £3.00 | |
| AC Fiorentina v Arsenal FC 14/09/1999 | View match | |
| Southampton FC v Arsenal FC 18/09/1999 | £3.50 | |
| Arsenal FC v AIK (Stockholm) 22/09/1999 | £5.00 | |
| Arsenal FC v Watford FC 25/09/1999 | £3.00 | |
| Arsenal FC v Watford FC 25/09/1999 | £2.00 | |
| Barcelona v Arsenal FC 29/09/1999 | View match | |
| West Ham United FC v Arsenal FC 03/10/1999 | £6.00 | |
| Arsenal FC v Preston North End FC 12/10/1999 | £4.50 |