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