| Barnsley FC v Birmingham City FC 20/11/1999 | View match | |
| Manchester City FC v Barnsley FC 24/11/1999 | £5.00 | |
| Queens Park Rangers FC v Barnsley FC 27/11/1999 | View match | |
| Tranmere Rovers FC v Barnsley FC 30/11/1999 | View match | |
| Barnsley FC v Charlton Athletic FC 04/12/1999 | View match | |
| Wimbledon v Barnsley FC 11/12/1999 | View match | |
| Barnsley FC v Walsall FC 18/12/1999 | View match | |
| Grimsby Town FC v Barnsley FC 26/12/1999 | View match | |
| Barnsley FC v Port Vale FC 28/12/1999 | View match | |
| West Bromwich Albion FC v Barnsley FC 03/01/2000 | View match | |
| Norwich City FC v Barnsley FC 08/01/2000 | View match | |
| Crystal Palace FC v Barnsley FC 15/01/2000 | View match |