| Middlesbrough FC v Charlton Athletic FC 10/04/1999 | £4.00 | |
| Charlton Athletic FC v Leeds United FC 17/04/1999 | £3.00 | |
| Charlton Athletic FC v Tottenham Hotspur FC 20/04/1999 | £4.50 | |
| Charlton Athletic FC v Tottenham Hotspur FC 20/04/1999 | £4.00 | |
| Everton FC v Charlton Athletic FC 24/04/1999 | View match | |
| 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 |