| Date | Opponents | Comp | Res | Venue |
|---|---|---|---|---|
| Sat 08 Aug 1998 | WATFORD | League | L 1-2 | Fratton Park |
| Tue 11 Aug 1998 | Plymouth Argyle | League Cup 1/1 | W 3-1 | Home Park |
| Sat 15 Aug 1998 | Tranmere Rovers | League | D 1-1 | Prenton Park |
| Tue 18 Aug 1998 | PLYMOUTH ARGYLE | League Cup 1/2 | W 3-2 | Fratton Park |
| Sat 22 Aug 1998 | IPSWICH TOWN | League | D 0-0 | Fratton Park |
| Sat 29 Aug 1998 | Huddersfield Town | League | D 3-3 | Kirklees Stadium |
| Mon 31 Aug 1998 | QUEENS PARK RANGERS | League | W 3-0 | Fratton Park |
| Sun 06 Sep 1998 | Oxford United | League | L 0-3 | Manor Ground |
| Tue 08 Sep 1998 | Bury | League | L 1-2 | Gigg Lane |
| Sat 12 Sep 1998 | SWINDON TOWN | League | W 5-2 | Fratton Park |
| Tue 15 Sep 1998 | WIMBLEDON | League Cup 2/1 | W 2-1 | Fratton Park |
| Sat 19 Sep 1998 | Port Vale | League | W 2-0 | Vale Park |
| Tue 22 Sep 1998 | Wimbledon | League Cup 2/2 | L 1-4* | Selhurst Park |
| Sat 26 Sep 1998 | SUNDERLAND | League | D 1-1 | Fratton Park |
| Tue 29 Sep 1998 | BIRMINGHAM CITY | League | L 0-1 | Fratton Park |
| Sat 03 Oct 1998 | Sheffield United | League | L 1-2 | Bramall Lane |
| Sat 10 Oct 1998 | Bristol City | League | D 2-2 | Ashton Gate |
| Sat 17 Oct 1998 | WOLVERHAMPTON WANDERERS | League | W 1-0 | Fratton Park |
| Tue 20 Oct 1998 | BRADFORD CITY | League | L 2-4 | Fratton Park |
| Sat 24 Oct 1998 | Barnsley | League | L 1-2 | Oakwell |
| Sat 07 Nov 1998 | Crystal Palace | League | L 1-4 | Selhurst Park |
| Tue 10 Nov 1998 | NORWICH CITY | League | L 1-2 | Fratton Park |
| Sat 14 Nov 1998 | Grimsby Town | League | D 1-1 | Blundell Park |
| Sat 21 Nov 1998 | WEST BROMWICH ALBION | League | W 2-1 | Fratton Park |
| Sat 28 Nov 1998 | Stockport County | League | L 0-2 | Edgeley Park |
| Sat 05 Dec 1998 | CREWE ALEXANDRA | League | W 2-0 | Fratton Park |
| Sun 13 Dec 1998 | GRIMSBY TOWN | League | L 0-1 | Fratton Park |
| Sat 19 Dec 1998 | Bolton Wanderers | League | L 1-3 | Burnden Way |
| Sat 26 Dec 1998 | Ipswich Town | League | L 0-3 | Portman Road |
| Mon 28 Dec 1998 | OXFORD UNITED | League | D 2-2 | Fratton Park |
| Sat 02 Jan 1999 | Nottingham Forest | F.A. Cup | W 1-0 | City Ground |
| Sat 09 Jan 1999 | Watford | League | D 0-0 | Vicarage Road |
| Sat 16 Jan 1999 | HUDDERSFIELD TOWN | League | W 1-0 | Fratton Park |
| Sat 23 Jan 1999 | LEEDS UNITED | F.A. Cup | L 1-5 | Fratton Park |
| Sat 30 Jan 1999 | Queens Park Rangers | League | D 1-1 | Loftus Road |
| Sat 06 Feb 1999 | TRANMERE ROVERS | League | D 1-1 | Fratton Park |
| Sat 13 Feb 1999 | BURY | League | W 2-1 | Fratton Park |
| Sat 20 Feb 1999 | Swindon Town | League | D 3-3 | County Ground |
| Sat 27 Feb 1999 | PORT VALE | League | W 4-0 | Fratton Park |
| Tue 02 Mar 1999 | Sunderland | League | L 0-2 | Stadium of Light |
| Sat 06 Mar 1999 | Birmingham City | League | L 1-4 | St. Andrews |
| Tue 09 Mar 1999 | SHEFFIELD UNITED | League | W 1-0 | Fratton Park |
| Sat 13 Mar 1999 | CRYSTAL PALACE | League | D 1-1 | Fratton Park |
| Sat 20 Mar 1999 | Norwich City | League | D 0-0 | Carrow Road |
| Sun 28 Mar 1999 | BARNSLEY | League | L 1-3 | Fratton Park |
| Sat 03 Apr 1999 | Wolverhampton Wanderers | League | L 0-2 | Molineux |
| Mon 05 Apr 1999 | BRISTOL CITY | League | L 0-1 | Fratton Park |
| Sat 10 Apr 1999 | Bradford City | League | L 1-2 | Valley Parade |
| Sat 17 Apr 1999 | West Bromwich Albion | League | D 2-2 | The Hawthorns |
| Sat 24 Apr 1999 | STOCKPORT COUNTY | League | W 3-1 | Fratton Park |
| Sat 01 May 1999 | Crewe Alexandra | League | L 1-3 | Gresty Road |
| Sun 09 May 1999 | BOLTON WANDERERS | League | L 0-2 | Fratton Park |
*after extra time, 90 minutes 2-1, Wimbledon won 5-3 on aggregate