1. Round 07/08/1999 Tranmere Rovers - Bolton Wanderers 0:0
2. Round 14/08/1999 Stockport County - Tranmere Rovers 2:1
3. Round 21/08/1999 Tranmere Rovers - Huddersfield Town 1:0
4. Round 28/08/1999 Port Vale FC - Tranmere Rovers 1:0
5. Round 30/08/1999 Tranmere Rovers - Sheffield United 1:3
6. Round 03/09/1999 Barnsley FC - Tranmere Rovers 3:0
7. Round 11/09/1999 Blackburn Rovers - Tranmere Rovers 2:0
8. Round 18/09/1999 Tranmere Rovers - Portsmouth FC 2:4
9. Round 25/09/1999 Tranmere Rovers - Charlton Athletic 2:2
10. Round 03/10/1999 Crewe Alexandra - Tranmere Rovers 0:2
11. Round 09/10/1999 Queens Park Rangers - Tranmere Rovers 2:1
12. Round 16/10/1999 Tranmere Rovers - Manchester City 1:1
16. Round 30/10/1999 Tranmere Rovers - Crewe Alexandra 2:0
17. Round 06/11/1999 Tranmere Rovers - West Bromwich Albion 3:0
19. Round 20/11/1999 Tranmere Rovers - Nottingham Forest 3:0 yellow card
20. Round 23/11/1999 Birmingham City - Tranmere Rovers 3:1
22. Round 04/12/1999 Bolton Wanderers - Tranmere Rovers 2:3 Goal
23. Round 17/12/1999 Tranmere Rovers - Norwich City 1:2
24. Round 26/12/1999 Walsall FC - Tranmere Rovers 1:2
25. Round 28/12/1999 Tranmere Rovers - Swindon Town 3:1
26. Round 03/01/2000 Fulham FC - Tranmere Rovers 1:0
27. Round 15/01/2000 Tranmere Rovers - Stockport County 0:0
28. Round 22/01/2000 Huddersfield Town - Tranmere Rovers 1:0
30. Round 05/02/2000 Sheffield United - Tranmere Rovers 3:1 Goal
32. Round 16/02/2000 Wolverhampton Wanderers - Tranmere Rovers 4:0
33. Round 01/03/2000 Portsmouth FC - Tranmere Rovers 1:2 yellow card
34. Round 04/03/2000 Tranmere Rovers - Blackburn Rovers 2:1
37. Round 18/03/2000 Nottingham Forest - Tranmere Rovers 1:1
39. Round 25/03/2000 Tranmere Rovers - Walsall FC 1:1
40. Round 01/04/2000 Norwich City - Tranmere Rovers 1:1
41. Round 09/04/2000 Tranmere Rovers - Fulham FC 1:1
42. Round 15/04/2000 Swindon Town - Tranmere Rovers 3:1
45. Round 29/04/2000 Grimsby Town - Tranmere Rovers 1:2
46. Round 07/05/2000 Tranmere Rovers - Crystal Palace 1:2 Goal