| Date | Opponents | Comp | Res | Venue |
|---|---|---|---|---|
| Sat 07 Aug 1999 | SHEFFIELD UNITED | League | W 2-0 | Fratton Park |
| Sat 14 Aug 1999 | Wolverhampton Wanderers | League | D 1-1 | Molineux |
| Tue 17 Aug 1999 | Torquay United | League Cup 1/1 | D 0-0 | Plainmoor |
| Sat 21 Aug 1999 | STOCKPORT COUNTY | League | W 2-0 | Fratton Park |
| Tue 24 Aug 1999 | TORQUAY UNITED | League Cup 1/2 | W 3-0 | Fratton Park |
| Sat 28 Aug 1999 | Barnsley | League | L 0-6 | Oakwell |
| Mon 30 Aug 1999 | HUDDERSFIELD TOWN | League | D 0-0 | Fratton Park |
| Sat 11 Sep 1999 | IPSWICH TOWN | League | D 1-1 | Fratton Park |
| Tue 14 Sep 1999 | BLACKBURN ROVERS | League Cup 2/1 | L 0-3 | Fratton Park |
| Sat 18 Sep 1999 | Tranmere Rovers | League | W 4-2 | Prenton Park |
| Wed 22 Sep 1999 | Blackburn Rovers | League Cup 2/2 | L 1-3 | Ewood Park |
| Sat 25 Sep 1999 | GRIMSBY TOWN | League | L 1-2 | Fratton Park |
| Sat 02 Oct 1999 | Crystal Palace | League | L 0-4 | Selhurst Park |
| Sat 16 Oct 1999 | CHARLTON ATHLETIC | League | L 0-2 | Fratton Park |
| Tue 19 Oct 1999 | WALSALL | League | W 5-1 | Fratton Park |
| Sat 23 Oct 1999 | Queens Park Rangers | League | D 0-0 | Loftus Road |
| Tue 26 Oct 1999 | Grimsby Town | League | L 0-1 | Blundell Park |
| Sat 30 Oct 1999 | CRYSTAL PALACE | League | W 3-1 | Fratton Park |
| Wed 03 Nov 1999 | Manchester City | League | L 2-4 | Maine Road |
| Sat 06 Nov 1999 | BIRMINGHAM CITY | League | D 2-2 | Fratton Park |
| Tue 09 Nov 1999 | Fulham | League | L 0-1 | Craven Cottage |
| Sun 14 Nov 1999 | West Bromwich Albion | League | L 2-3 | The Hawthorns |
| Sat 20 Nov 1999 | CREWE ALEXANDRA | League | L 0-2 | Fratton Park |
| Wed 24 Nov 1999 | Nottingham Forest | League | L 0-2 | City Ground |
| Sat 27 Nov 1999 | BOLTON WANDERERS | League | D 0-0 | Fratton Park |
| Sat 04 Dec 1999 | Sheffield United | League | L 0-1 | Bramall Lane |
| Sat 11 Dec 1999 | Sunderland | F.A. Cup | L 0-1 | Stadium of Light |
| Sat 18 Dec 1999 | PORT VALE | League | D 0-0 | Fratton Park |
| Sun 26 Dec 1999 | Swindon Town | League | D 1-1 | County Ground |
| Tue 28 Dec 1999 | BLACKBURN ROVERS | League | L 1-2 | Fratton Park |
| Mon 03 Jan 2000 | Norwich City | League | L 1-2 | Carrow Road |
| Sat 15 Jan 2000 | WOLVERHAMPTON WANDERERS | League | L 2-3 | Fratton Park |
| Sat 22 Jan 2000 | Stockport County | League | D 1-1 | Edgeley Park |
| Sat 29 Jan 2000 | BARNSLEY | League | W 3-0 | Fratton Park |
| Sat 05 Feb 2000 | Huddersfield Town | League | W 1-0 | Kirklees Stadium |
| Sat 12 Feb 2000 | FULHAM | League | L 0-1 | Fratton Park |
| Tue 22 Feb 2000 | Bolton Wanderers | League | L 0-3 | Burnden Way |
| Wed 01 Mar 2000 | TRANMERE ROVERS | League | L 1-2 | Fratton Park |
| Sat 04 Mar 2000 | Ipswich Town | League | W 1-0 | Portman Road |
| Tue 07 Mar 2000 | Birmingham City | League | L 0-1 | St. Andrews |
| Sat 11 Mar 2000 | NOTTINGHAM FOREST | League | W 2-1 | Fratton Park |
| Sat 18 Mar 2000 | Crewe Alexandra | League | W 3-1 | Gresty Road |
| Tue 21 Mar 2000 | WEST BROMWICH ALBION | League | W 2-0 | Fratton Park |
| Sat 25 Mar 2000 | SWINDON TOWN | League | W 4-1 | Fratton Park |
| Sat 01 Apr 2000 | Port Vale | League | L 0-2 | Vale Park |
| Sat 08 Apr 2000 | NORWICH CITY | League | W 2-1 | Fratton Park |
| Sat 15 Apr 2000 | Blackburn Rovers | League | D 1-1 | Ewood Park |
| Fri 21 Apr 2000 | Charlton Athletic | League | D 1-1 | The Valley |
| Mon 24 Apr 2000 | MANCHESTER CITY | League | D 2-2 | Fratton Park |
| Sat 29 Apr 2000 | Walsall | League | L 0-1 | Bescot Stadium |
| Sun 07 May 2000 | QUEENS PARK RANGERS | League | L 1-3 | Fratton Park |
