| AFC Bournemouth v Stoke City FC 16/10/1999 | View match | |
| AFC Bournemouth v Bristol Rovers FC 19/10/1999 | View match | |
| Bury FC v AFC Bournemouth 23/10/1999 | £5.00 | |
| Notts County FC v AFC Bournemouth 30/10/1999 | View match | |
| Preston North End FC v AFC Bournemouth 03/11/1999 | View match | |
| AFC Bournemouth v Cardiff City FC 06/11/1999 | View match | |
| AFC Bournemouth v Notts County FC 09/11/1999 | View match | |
| Gillingham FC v AFC Bournemouth 12/11/1999 | View match | |
| Wigan Athletic FC v AFC Bournemouth 16/11/1999 | View match | |
| AFC Bournemouth v Bristol City FC 20/11/1999 | View match | |
| AFC Bournemouth v Brentford FC 23/11/1999 | View match | |
| AFC Bournemouth v Millwall FC 27/11/1999 | View match |