| AFC Bournemouth v Luton Town FC 31/08/1999 | View match | |
| Luton Town FC v Bury FC 04/09/1999 | £4.00 | |
| Luton Town FC v Wrexham FC 11/09/1999 | £6.00 | |
| Brentford FC v Luton Town FC 18/09/1999 | View match | |
| Luton Town FC v Oxford United FC 25/09/1999 | View match | |
| Wigan Athletic FC v Luton Town FC 02/10/1999 | View match | |
| Oldham Athletic FC v Luton Town FC 09/10/1999 | View match | |
| Luton Town FC v Gillingham FC 16/10/1999 | View match | |
| Luton Town FC v Wycombe Wanderers FC 19/10/1999 | £5.00 | |
| Oxford United FC v Luton Town FC 23/10/1999 | View match | |
| Luton Town FC v Kingstonian FC 30/10/1999 | £6.00 | |
| Millwall FC v Luton Town FC 02/11/1999 | View match |