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 yellow card
4. Round 28/08/1999 Port Vale FC - Tranmere Rovers 1:0
5. Round 30/08/1999 Tranmere Rovers - Sheffield United 1:3 yellow card
6. Round 03/09/1999 Barnsley FC - Tranmere Rovers 3:0
8. Round 18/09/1999 Tranmere Rovers - Portsmouth FC 2:4 Goal
9. Round 25/09/1999 Tranmere Rovers - Charlton Athletic 2:2
12. Round 16/10/1999 Tranmere Rovers - Manchester City 1:1
17. Round 06/11/1999 Tranmere Rovers - West Bromwich Albion 3:0
19. Round 20/11/1999 Tranmere Rovers - Nottingham Forest 3:0 Goal
20. Round 23/11/1999 Birmingham City - Tranmere Rovers 3:1
21. Round 27/11/1999 Tranmere Rovers - Wolverhampton Wanderers 1:0
22. Round 04/12/1999 Bolton Wanderers - Tranmere Rovers 2:3
23. Round 17/12/1999 Tranmere Rovers - Norwich City 1:2
24. Round 26/12/1999 Walsall FC - Tranmere Rovers 1:2
26. Round 03/01/2000 Fulham FC - Tranmere Rovers 1:0
30. Round 05/02/2000 Sheffield United - Tranmere Rovers 3:1
31. Round 11/02/2000 Tranmere Rovers - Barnsley FC 2:2 Goal
34. Round 04/03/2000 Tranmere Rovers - Blackburn Rovers 2:1
35. Round 07/03/2000 West Bromwich Albion - Tranmere Rovers 2:0
36. Round 11/03/2000 Tranmere Rovers - Birmingham City 2:1
37. Round 18/03/2000 Nottingham Forest - Tranmere Rovers 1:1
38. Round 22/03/2000 Tranmere Rovers - Ipswich Town 0:2
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 Goal
42. Round 15/04/2000 Swindon Town - Tranmere Rovers 3:1
29. Round 18/04/2000 Tranmere Rovers - Port Vale FC 2:1 GoalGoal
43. Round 22/04/2000 Manchester City - Tranmere Rovers 2:0
44. Round 24/04/2000 Tranmere Rovers - Queens Park Rangers 1:1
45. Round 29/04/2000 Grimsby Town - Tranmere Rovers 1:2