| Blackpool FC v AFC Bournemouth 18/09/1999 | View match | |
| AFC Bournemouth v Charlton Athletic FC 21/09/1999 | View match | |
| AFC Bournemouth v Bury FC 25/09/1999 | £6.50 | |
| Chesterfield FC v AFC Bournemouth 02/10/1999 | View match | |
| West Ham United FC v AFC Bournemouth 13/10/1999 | View match | |
| 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 |