7. Round | 10/09/1999 | Barnsley FC | - | Stockport County | 2:1 | ||||
8. Round | 18/09/1999 | Bolton Wanderers | - | Barnsley FC | 2:2 | ||||
9. Round | 25/09/1999 | Barnsley FC | - | Huddersfield Town | 4:2 | ||||
10. Round | 01/10/1999 | Nottingham Forest | - | Barnsley FC | 3:0 | ||||
25. Round | 28/12/1999 | Barnsley FC | - | Port Vale FC | 3:1 | ||||
28. Round | 22/01/2000 | Barnsley FC | - | Blackburn Rovers | 5:1 | ||||
31. Round | 11/02/2000 | Tranmere Rovers | - | Barnsley FC | 2:2 | ||||
32. Round | 19/02/2000 | Barnsley FC | - | Queens Park Rangers | 1:1 | ||||
33. Round | 26/02/2000 | Barnsley FC | - | Bolton Wanderers | 1:1 | ||||
39. Round | 27/03/2000 | Barnsley FC | - | Grimsby Town | 3:0 |