9. Round 25/09/1999 Bolton Wanderers - Nottingham Forest 3:2
10. Round 02/10/1999 Swindon Town - Bolton Wanderers 0:4
11. Round 09/10/1999 Wolverhampton Wanderers - Bolton Wanderers 1:0
12. Round 16/10/1999 Bolton Wanderers - Huddersfield Town 1:0
13. Round 19/10/1999 Bolton Wanderers - Crewe Alexandra 2:2
14. Round 24/10/1999 Norwich City - Bolton Wanderers 2:1
17. Round 06/11/1999 Bolton Wanderers - Crystal Palace 2:0
18. Round 14/11/1999 Sheffield United - Bolton Wanderers 1:2
19. Round 20/11/1999 Bolton Wanderers - Grimsby Town 2:0 yellow card
20. Round 23/11/1999 Fulham FC - Bolton Wanderers 1:1
21. Round 27/11/1999 Portsmouth FC - Bolton Wanderers 0:0
22. Round 04/12/1999 Bolton Wanderers - Tranmere Rovers 2:3 yellow card
5. Round 07/12/1999 Blackburn Rovers - Bolton Wanderers 3:1
23. Round 18/12/1999 Bolton Wanderers - Stockport County 0:1
25. Round 28/12/1999 Bolton Wanderers - West Bromwich Albion 1:1
26. Round 03/01/2000 Walsall FC - Bolton Wanderers 2:0
32. Round 22/02/2000 Bolton Wanderers - Portsmouth FC 3:0
33. Round 26/02/2000 Barnsley FC - Bolton Wanderers 1:1
34. Round 04/03/2000 Bolton Wanderers - Charlton Athletic 0:2
35. Round 07/03/2000 Crystal Palace - Bolton Wanderers 0:0
36. Round 11/03/2000 Bolton Wanderers - Fulham FC 3:1
40. Round 14/03/2000 Stockport County - Bolton Wanderers 0:0
38. Round 21/03/2000 Bolton Wanderers - Sheffield United 2:0
39. Round 25/03/2000 Bolton Wanderers - Port Vale FC 2:1
29. Round 05/04/2000 Manchester City - Bolton Wanderers 2:0
41. Round 08/04/2000 Bolton Wanderers - Walsall FC 4:3
42. Round 15/04/2000 West Bromwich Albion - Bolton Wanderers 4:4
43. Round 22/04/2000 Huddersfield Town - Bolton Wanderers 0:3
45. Round 29/04/2000 Crewe Alexandra - Bolton Wanderers 1:3
44. Round 03/05/2000 Bolton Wanderers - Wolverhampton Wanderers 2:1
46. Round 07/05/2000 Bolton Wanderers - Norwich City 1:0