| Bolton Wanderers FC v Barnsley FC 18/09/1999 | View match | |
| Stockport County FC v Barnsley FC 21/09/1999 | View match | |
| Barnsley FC v Huddersfield Town FC 25/09/1999 | View match | |
| Nottingham Forest FC v Barnsley FC 01/10/1999 | View match | |
| Bradford City FC v Barnsley FC 12/10/1999 | View match | |
| Barnsley FC v Wolverhampton Wanderers FC 16/10/1999 | View match | |
| Barnsley FC v Swindon Town FC 19/10/1999 | View match | |
| Crewe Alexandra FC v Barnsley FC 23/10/1999 | View match | |
| Huddersfield Town FC v Barnsley FC 26/10/1999 | View match | |
| Barnsley FC v Nottingham Forest FC 30/10/1999 | View match | |
| Barnsley FC v Sheffield United FC 06/11/1999 | View match | |
| Fulham FC v Barnsley FC 13/11/1999 | £4.50 |