| Luton Town FC v Blackpool FC 14/08/1999 | £5.00 | |
| Reading FC v Luton Town FC 21/08/1999 | View match | |
| Bristol Rovers FC v Luton Town FC 25/08/1999 | View match | |
| Luton Town FC v Cardiff City FC 28/08/1999 | £5.00 | |
| 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 |