Portsmouth
1998-1999
[squad stats] [appearance chart]
| Date | K.O. | Comp | Opponents | Ven | Res | Att | ||||
| Sat 8th Aug | --:-- | FL1 | Watford | H | L | 1-2 |  |
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| Tue 11th Aug | --:-- | LC | Plymouth Argyle | A | W | 3-1 | |
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| Sat 15th Aug | --:-- | FL1 | Tranmere Rovers | A | D | 1-1 | |
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| Tue 18th Aug | --:-- | LC | Plymouth Argyle | H | W | 3-2 | |
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| Sat 22nd Aug | --:-- | FL1 | Ipswich Town | H | D | 0-0 | |
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| Sat 29th Aug | --:-- | FL1 | Huddersfield Town | A | D | 3-3 | |
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| Mon 31st Aug | --:-- | FL1 | Queens Park Rangers | H | W | 3-0 | |
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| Sun 6th Sep | --:-- | FL1 | Oxford United | A | L | 0-3 | |
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| Tue 8th Sep | --:-- | FL1 | Bury | A | L | 1-2 | |
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| Sat 12th Sep | --:-- | FL1 | Swindon Town | H | W | 5-2 | |
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| Tue 15th Sep | --:-- | LC | Wimbledon | H | W | 2-1 | |
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| Sat 19th Sep | --:-- | FL1 | Port Vale | A | W | 2-0 | |
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| Tue 22nd Sep | --:-- | LC | Wimbledon | A | L | 1-4 | |
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| Sat 26th Sep | --:-- | FL1 | Sunderland | H | D | 1-1 | |
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| Tue 29th Sep | --:-- | FL1 | Birmingham City | H | L | 0-1 | |
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| Sat 3rd Oct | --:-- | FL1 | Sheffield United | A | L | 1-2 | |
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| Sat 10th Oct | --:-- | FL1 | Bristol City | A | D | 2-2 | |
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| Sat 17th Oct | --:-- | FL1 | Wolverhampton Wanderers | H | W | 1-0 | |
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| Tue 20th Oct | --:-- | FL1 | Bradford City | H | L | 2-4 | |
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| Sat 24th Oct | --:-- | FL1 | Barnsley | A | L | 1-2 | |
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| Sat 7th Nov | --:-- | FL1 | Crystal Palace | A | L | 1-4 | |
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| Tue 10th Nov | --:-- | FL1 | Norwich City | H | L | 1-2 | |
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| Sat 14th Nov | --:-- | FL1 | Grimsby Town | A | D | 1-1 | |
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| Sat 21st Nov | --:-- | FL1 | West Bromwich Albion | H | W | 2-1 | |
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| Sat 28th Nov | --:-- | FL1 | Stockport County | A | L | 0-2 | |
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| Sat 5th Dec | --:-- | FL1 | Crewe Alexandra | H | W | 2-0 | |
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| Sun 13th Dec | --:-- | FL1 | Grimsby Town | H | L | 0-1 | |
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| Sat 19th Dec | --:-- | FL1 | Bolton Wanderers | A | L | 1-3 | |
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| Sat 26th Dec | --:-- | FL1 | Ipswich Town | A | L | 0-3 | |
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| Mon 28th Dec | --:-- | FL1 | Oxford United | H | D | 2-2 | |
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| Sat 2nd Jan | --:-- | FAC | Nottingham Forest | A | W | 1-0 | |
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| Sat 9th Jan | --:-- | FL1 | Watford | A | D | 0-0 | |
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| Sat 16th Jan | --:-- | FL1 | Huddersfield Town | H | W | 1-0 | |
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| Sat 23rd Jan | --:-- | FAC | Leeds United | H | L | 1-5 | |
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| Sat 30th Jan | --:-- | FL1 | Queens Park Rangers | A | D | 1-1 | |
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| Sat 6th Feb | --:-- | FL1 | Tranmere Rovers | H | D | 1-1 | |
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| Sat 13th Feb | --:-- | FL1 | Bury | H | W | 2-1 | |
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| Sat 20th Feb | --:-- | FL1 | Swindon Town | A | D | 3-3 | |
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| Sat 27th Feb | --:-- | FL1 | Port Vale | H | W | 4-0 | |
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| Tue 2nd Mar | --:-- | FL1 | Sunderland | A | L | 0-2 | |
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| Sat 6th Mar | --:-- | FL1 | Birmingham City | A | L | 1-4 | |
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| Tue 9th Mar | --:-- | FL1 | Sheffield United | H | W | 1-0 | |
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| Sat 13th Mar | --:-- | FL1 | Crystal Palace | H | D | 1-1 | |
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| Sat 20th Mar | --:-- | FL1 | Norwich City | A | D | 0-0 | |
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| Sun 28th Mar | --:-- | FL1 | Barnsley | H | L | 1-3 | |
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| Sat 3rd Apr | --:-- | FL1 | Wolverhampton Wanderers | A | L | 0-2 | |
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| Mon 5th Apr | --:-- | FL1 | Bristol City | H | L | 0-1 | |
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| Sat 10th Apr | --:-- | FL1 | Bradford City | A | L | 1-2 | |
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| Sat 17th Apr | --:-- | FL1 | West Bromwich Albion | A | D | 2-2 | |
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| Sat 24th Apr | --:-- | FL1 | Stockport County | H | W | 3-1 | |
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| Sat 1st May | --:-- | FL1 | Crewe Alexandra | A | L | 1-3 | |
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| Sun 9th May | --:-- | FL1 | Bolton Wanderers | H | L | 0-2 | |