1. Round 07/08/1998 Portsmouth FC - Watford FC 1:2
4. Round 28/08/1998 Huddersfield Town - Portsmouth FC 3:3
5. Round 30/08/1998 Portsmouth FC - Queens Park Rangers 3:0
6. Round 05/09/1998 Oxford United - Portsmouth FC 3:0
7. Round 07/09/1998 Bury FC - Portsmouth FC 2:1
8. Round 11/09/1998 Portsmouth FC - Swindon Town 5:2
9. Round 18/09/1998 Port Vale FC - Portsmouth FC 0:2
10. Round 25/09/1998 Portsmouth FC - Sunderland AFC 1:1
11. Round 28/09/1998 Portsmouth FC - Birmingham City 0:1
12. Round 02/10/1998 Sheffield United - Portsmouth FC 2:1
13. Round 09/10/1998 Bristol City - Portsmouth FC 2:2
14. Round 16/10/1998 Portsmouth FC - Wolverhampton Wanderers 1:0
15. Round 19/10/1998 Portsmouth FC - Bradford City 2:4
16. Round 23/10/1998 Barnsley FC - Portsmouth FC 2:1
18. Round 06/11/1998 Crystal Palace - Portsmouth FC 4:1
17. Round 09/11/1998 Portsmouth FC - Norwich City 1:2
19. Round 13/11/1998 Grimsby Town - Portsmouth FC 1:1
20. Round 20/11/1998 Portsmouth FC - West Bromwich Albion 2:1
21. Round 27/11/1998 Stockport County - Portsmouth FC 2:0
22. Round 04/12/1998 Portsmouth FC - Crewe Alexandra 2:0
23. Round 12/12/1998 Portsmouth FC - Grimsby Town 0:1
24. Round 18/12/1998 Bolton Wanderers - Portsmouth FC 3:1
25. Round 25/12/1998 Ipswich Town - Portsmouth FC 3:0
26. Round 27/12/1998 Portsmouth FC - Oxford United 2:2
31. Round 12/02/1999 Portsmouth FC - Bury FC 2:1
32. Round 19/02/1999 Swindon Town - Portsmouth FC 3:3
33. Round 26/02/1999 Portsmouth FC - Port Vale FC 4:0
34. Round 01/03/1999 Sunderland AFC - Portsmouth FC 2:0
35. Round 05/03/1999 Birmingham City - Portsmouth FC 4:1
39. Round 27/03/1999 Portsmouth FC - Barnsley FC 1:3
40. Round 02/04/1999 Wolverhampton Wanderers - Portsmouth FC 2:0
42. Round 09/04/1999 Bradford City - Portsmouth FC 2:1
43. Round 16/04/1999 West Bromwich Albion - Portsmouth FC 2:2
46. Round 08/05/1999 Portsmouth FC - Bolton Wanderers 0:2