| Charlton Athletic FC v Blackburn Rovers FC 01/05/1999 | £4.00 | |
| Aston Villa FC v Charlton Athletic FC 08/05/1999 | View match | |
| Charlton Athletic FC v Sheffield Wednesday FC 16/05/1999 | £3.00 | |
| Plymouth Argyle FC v Charlton Athletic FC 21/07/1999 | View match | |
| Torquay United FC v Charlton Athletic FC 23/07/1999 | View match | |
| Barnet FC v Charlton Athletic FC 26/07/1999 | View match | |
| Leyton Orient FC v Charlton Athletic FC 27/07/1999 | View match | |
| Charlton Athletic FC v West Ham United FC 30/07/1999 | £6.00 | |
| Welling United v Charlton Athletic FC 03/08/1999 | View match | |
| Charlton Athletic FC v Barnsley FC 07/08/1999 | £5.50 | |
| Charlton Athletic FC v Norwich City FC 21/08/1999 | £4.00 | |
| Fulham FC v Charlton Athletic FC 28/08/1999 | £4.00 |