| Charlton Athletic FC v Bolton Wanderers FC 11/09/1999 | £4.50 | |
| Charlton Athletic FC v AFC Bournemouth 14/09/1999 | £5.50 | |
| Sheffield United FC v Charlton Athletic FC 18/09/1999 | View match | |
| AFC Bournemouth v Charlton Athletic FC 21/09/1999 | View match | |
| Tranmere Rovers FC v Charlton Athletic FC 25/09/1999 | View match | |
| Charlton Athletic FC v Stockport County FC 28/09/1999 | £4.00 | |
| Charlton Athletic FC v Birmingham City FC 02/10/1999 | £3.00 | |
| Welling United v Charlton Athletic FC 11/10/1999 | View match | |
| Portsmouth FC v Charlton Athletic FC 16/10/1999 | View match | |
| Ipswich Town FC v Charlton Athletic FC 19/10/1999 | View match | |
| Charlton Athletic FC v West Bromwich Albion FC 23/10/1999 | £4.50 | |
| Charlton Athletic FC v Tranmere Rovers FC 26/10/1999 | £5.00 |