| Arsenal FC v Preston North End FC 12/10/1999 | View match | |
| Arsenal FC v Everton FC 16/10/1999 | £2.00 | |
| Arsenal FC v Everton FC 16/10/1999 | £4.00 | |
| Arsenal FC v Barcelona 19/10/1999 | View match | |
| Chelsea FC v Arsenal FC 23/10/1999 | £2.50 | |
| Chelsea FC v Arsenal FC 23/10/1999 | £3.00 | |
| Arsenal FC v AC Fiorentina 27/10/1999 | £4.00 | |
| Arsenal FC v Newcastle United FC 30/10/1999 | £2.50 | |
| Arsenal FC v Newcastle United FC 30/10/1999 | £3.50 | |
| AIK (Stockholm) v Arsenal FC 02/11/1999 | View match | |
| Tottenham Hotspur FC v Arsenal FC 07/11/1999 | £5.00 | |
| Arsenal FC v Real Madrid 08/11/1999 | £5.00 |