| 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 | |
| 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 |