| Birmingham City FC v Charlton Athletic FC 30/10/1999 | View match | |
| Crewe Alexandra FC v Charlton Athletic FC 02/11/1999 | View match | |
| Charlton Athletic FC v Walsall FC 06/11/1999 | £4.50 | |
| Grimsby Town FC v Charlton Athletic FC 12/11/1999 | View match | |
| Charlton Athletic FC v Manchester City FC 20/11/1999 | £5.50 | |
| Swindon Town FC v Charlton Athletic FC 23/11/1999 | View match | |
| Charlton Athletic FC v Port Vale FC 27/11/1999 | £4.50 | |
| Charlton Athletic FC v Blackburn Rovers FC 30/11/1999 | £4.00 | |
| Barnsley FC v Charlton Athletic FC 04/12/1999 | View match | |
| Charlton Athletic FC v Swindon Town FC 11/12/1999 | £4.50 | |
| Queens Park Rangers FC v Charlton Athletic FC 18/12/1999 | View match | |
| Charlton Athletic FC v Crystal Palace FC 26/12/1999 | £4.50 |