| Reading FC v Chesterfield FC 18/09/1999 | View match | |
| Reading FC v Bradford City FC 22/09/1999 | View match | |
| Reading FC v Oldham Athletic FC 25/09/1999 | View match | |
| Wycombe Wanderers FC v Reading FC 02/10/1999 | View match | |
| Stoke City FC v Reading FC 09/10/1999 | View match | |
| Reading FC v Wigan Athletic FC 16/10/1999 | View match | |
| Reading FC v Bury FC 20/10/1999 | £6.50 | |
| Oldham Athletic FC v Reading FC 23/10/1999 | View match | |
| Reading FC v Yeovil Town FC 30/10/1999 | View match | |
| Brentford FC v Reading FC 02/11/1999 | View match | |
| Reading FC v Oxford United FC 07/11/1999 | View match | |
| Millwall FC v Reading FC 16/11/1999 | View match |