| Arsenal FC v Aston Villa FC 11/09/1999 | £3.50 | |
| Southampton FC v Arsenal FC 18/09/1999 | £3.50 | |
| Arsenal FC v Watford FC 25/09/1999 | £3.00 | |
| Arsenal FC v Watford FC 25/09/1999 | £2.00 | |
| Arsenal FC v Preston North End FC 12/10/1999 | £4.50 | |
| Arsenal FC v Everton FC 16/10/1999 | £4.00 | |
| Arsenal FC v Everton FC 16/10/1999 | £2.00 | |
| Chelsea FC v Arsenal FC 23/10/1999 | £3.00 | |
| Chelsea FC v Arsenal FC 23/10/1999 | £2.50 | |
| 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 |