| Barnsley FC v Watford FC 01/05/1999 | View match | |
| Swindon Town FC v Barnsley FC 09/05/1999 | View match | |
| Charlton Athletic FC v Barnsley FC 07/08/1999 | £5.50 | |
| Lincoln City FC v Barnsley FC 10/08/1999 | View match | |
| Barnsley FC v Crystal Palace FC 14/08/1999 | View match | |
| Blackburn Rovers FC v Barnsley FC 21/08/1999 | View match | |
| Barnsley FC v Lincoln City FC 24/08/1999 | View match | |
| Barnsley FC v Portsmouth FC 28/08/1999 | View match | |
| Ipswich Town FC v Barnsley FC 30/08/1999 | View match | |
| Barnsley FC v Tranmere Rovers FC 03/09/1999 | View match | |
| Barnsley FC v Stockport County FC 10/09/1999 | View match | |
| Barnsley FC v Stockport County FC 14/09/1999 | View match |