1. Round 07/08/1999 Tranmere Rovers - Bolton Wanderers 0:0
2. Round 14/08/1999 Bolton Wanderers - Queens Park Rangers 2:1
3. Round 21/08/1999 Ipswich Town - Bolton Wanderers 1:0
4. Round 28/08/1999 Bolton Wanderers - Manchester City 0:1 yellow card
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 Goal
9. Round 25/09/1999 Bolton Wanderers - Nottingham Forest 3:2 Goal
10. Round 02/10/1999 Swindon Town - Bolton Wanderers 0:4 Goal
11. Round 09/10/1999 Wolverhampton Wanderers - Bolton Wanderers 1:0
12. Round 16/10/1999 Bolton Wanderers - Huddersfield Town 1:0 Goal
13. Round 19/10/1999 Bolton Wanderers - Crewe Alexandra 2:2
14. Round 24/10/1999 Norwich City - Bolton Wanderers 2:1 Goal
15. Round 27/10/1999 Nottingham Forest - Bolton Wanderers 1:1
16. Round 30/10/1999 Bolton Wanderers - Swindon Town 2:0
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
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
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
28. Round 22/01/2000 Bolton Wanderers - Ipswich Town 1:1
30. Round 05/02/2000 Bolton Wanderers - Blackburn Rovers 3:1
32. Round 22/02/2000 Bolton Wanderers - Portsmouth FC 3:0
33. Round 26/02/2000 Barnsley FC - Bolton Wanderers 1:1