3. Round 21/08/1999 Ipswich Town - Bolton Wanderers 1:0
4. Round 28/08/1999 Bolton Wanderers - Manchester City 0:1
6. Round 05/09/1999 Bolton Wanderers - Birmingham City 3:3
7. Round 11/09/1999 Charlton Athletic - Bolton Wanderers 2:1
8. Round 18/09/1999 Bolton Wanderers - Barnsley FC 2:2
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
15. Round 27/10/1999 Nottingham Forest - Bolton Wanderers 1:1
16. Round 30/10/1999 Bolton Wanderers - Swindon Town 2:0 Goal
18. Round 14/11/1999 Sheffield United - Bolton Wanderers 1:2
20. Round 23/11/1999 Fulham FC - Bolton Wanderers 1:1 yellow card
21. Round 27/11/1999 Portsmouth FC - Bolton Wanderers 0:0
22. Round 04/12/1999 Bolton Wanderers - Tranmere Rovers 2:3 Goal
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
27. Round 15/01/2000 Queens Park Rangers - Bolton Wanderers 0:1
30. Round 05/02/2000 Bolton Wanderers - Blackburn Rovers 3:1
24. Round 08/02/2000 Port Vale FC - Bolton Wanderers 0:1
31. Round 12/02/2000 Birmingham City - Bolton Wanderers 2:1
32. Round 22/02/2000 Bolton Wanderers - Portsmouth FC 3:0 Goal
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
40. Round 14/03/2000 Stockport County - Bolton Wanderers 0:0