1. Round 07/08/1999 Charlton Athletic - Barnsley FC 3:1
3. Round 21/08/1999 Blackburn Rovers - Barnsley FC 1:2
6. Round 03/09/1999 Barnsley FC - Tranmere Rovers 3:0
7. Round 10/09/1999 Barnsley FC - Stockport County 2:1
9. Round 25/09/1999 Barnsley FC - Huddersfield Town 4:2
12. Round 16/10/1999 Barnsley FC - Wolverhampton Wanderers 1:2
13. Round 19/10/1999 Barnsley FC - Swindon Town 1:0
14. Round 23/10/1999 Crewe Alexandra - Barnsley FC 0:1
15. Round 26/10/1999 Huddersfield Town - Barnsley FC 2:1
16. Round 30/10/1999 Barnsley FC - Nottingham Forest 1:0
17. Round 06/11/1999 Barnsley FC - Sheffield United 2:0
18. Round 13/11/1999 Fulham FC - Barnsley FC 1:3
19. Round 20/11/1999 Barnsley FC - Birmingham City 2:1 Goal
20. Round 24/11/1999 Manchester City - Barnsley FC 3:1
22. Round 04/12/1999 Barnsley FC - Charlton Athletic 1:1
23. Round 18/12/1999 Barnsley FC - Walsall FC 3:2
24. Round 26/12/1999 Grimsby Town - Barnsley FC 0:3
25. Round 28/12/1999 Barnsley FC - Port Vale FC 3:1 Goal
26. Round 03/01/2000 West Bromwich Albion - Barnsley FC 0:2 yellow card
11. Round 08/01/2000 Norwich City - 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 Goal
34. Round 03/03/2000 Stockport County - Barnsley FC 1:3
35. Round 07/03/2000 Sheffield United - Barnsley FC 3:3
36. Round 11/03/2000 Barnsley FC - Manchester City 2:1
37. Round 18/03/2000 Birmingham City - Barnsley FC 3:1
38. Round 21/03/2000 Barnsley FC - Fulham FC 1:0
39. Round 27/03/2000 Barnsley FC - Grimsby Town 3:0 Goal
40. Round 01/04/2000 Walsall FC - Barnsley FC 1:4 yellow card
41. Round 08/04/2000 Barnsley FC - West Bromwich Albion 2:2
42. Round 15/04/2000 Port Vale FC - Barnsley FC 2:2
43. Round 22/04/2000 Wolverhampton Wanderers - Barnsley FC 2:0
44. Round 24/04/2000 Barnsley FC - Norwich City 2:1