Portsmouth
1999-2000
[squad stats] [appearance chart]
| Date | K.O. | Comp | Opponents | Ven | Res | Att | ||||
| Sat 7th Aug | --:-- | FL1 | Sheffield United | H | W | 2-0 | 17667 |  |
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| Sat 14th Aug | --:-- | FL1 | Wolverhampton Wanderers | A | D | 1-1 | 21024 | |
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| Tue 17th Aug | --:-- | LC | Torquay United | A | D | 0-0 | |
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| Sat 21st Aug | --:-- | FL1 | Stockport County | H | W | 2-0 | 15002 | |
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| Tue 24th Aug | --:-- | LC | Torquay United | H | W | 3-0 | |
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| Sat 28th Aug | --:-- | FL1 | Barnsley | A | L | 0-6 | 13792 | |
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| Mon 30th Aug | --:-- | FL1 | Huddersfield Town | H | D | 0-0 | 13105 | |
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| Sat 11th Sep | --:-- | FL1 | Ipswich Town | H | D | 1-1 | 16034 | |
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| Tue 14th Sep | --:-- | LC | Blackburn Rovers | H | L | 0-3 | |
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| Sat 18th Sep | --:-- | FL1 | Tranmere Rovers | A | W | 4-2 | 5870 | |
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| Wed 22nd Sep | --:-- | LC | Blackburn Rovers | A | L | 1-3 | |
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| Sat 25th Sep | --:-- | FL1 | Grimsby Town | H | L | 1-2 | 12073 | |
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| Sat 2nd Oct | --:-- | FL1 | Crystal Palace | A | L | 0-4 | 15221 | |
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| Sat 16th Oct | --:-- | FL1 | Charlton Athletic | H | L | 0-2 | 14812 | |
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| Tue 19th Oct | --:-- | FL1 | Walsall | H | W | 5-1 | 9042 | |
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| Sat 23rd Oct | --:-- | FL1 | Queens Park Rangers | A | D | 0-0 | 13303 | |
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| Tue 26th Oct | --:-- | FL1 | Grimsby Town | A | L | 0-1 | 5912 | |
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| Sat 30th Oct | --:-- | FL1 | Crystal Palace | H | W | 3-1 | 13018 | |
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| Wed 3rd Nov | --:-- | FL1 | Manchester City | A | L | 2-4 | 31660 | |
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| Sat 6th Nov | --:-- | FL1 | Birmingham City | H | D | 2-2 | 12756 | |
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| Tue 9th Nov | --:-- | FL1 | Fulham | A | L | 0-1 | 13229 | |
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| Sun 14th Nov | --:-- | FL1 | West Bromwich Albion | A | L | 2-3 | 11483 | |
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| Sat 20th Nov | --:-- | FL1 | Crewe Alexandra | H | L | 0-2 | 11550 | |
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| Wed 24th Nov | --:-- | FL1 | Nottingham Forest | A | L | 0-2 | 13841 | |
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| Sat 27th Nov | --:-- | FL1 | Bolton Wanderers | H | D | 0-0 | 10431 | |
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| Sat 4th Dec | --:-- | FL1 | Sheffield United | A | L | 0-1 | 10834 | |
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| Sat 11th Dec | --:-- | FAC | Sunderland | A | L | 0-1 | |
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| Sat 18th Dec | --:-- | FL1 | Port Vale | H | D | 0-0 | 11869 | |
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| Sun 26th Dec | --:-- | FL1 | Swindon Town | A | D | 1-1 | 10279 | |
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| Tue 28th Dec | --:-- | FL1 | Blackburn Rovers | H | L | 1-2 | 15208 | |
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| Mon 3rd Jan | --:-- | FL1 | Norwich City | A | L | 1-2 | 16637 | |
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| Sat 15th Jan | --:-- | FL1 | Wolverhampton Wanderers | H | L | 2-3 | 13255 | |
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| Sat 22nd Jan | --:-- | FL1 | Stockport County | A | D | 1-1 | 8008 | |
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| Sat 29th Jan | --:-- | FL1 | Barnsley | H | W | 3-0 | 12201 | |
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| Sat 5th Feb | --:-- | FL1 | Huddersfield Town | A | W | 1-0 | 12753 | |
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| Sat 12th Feb | --:-- | FL1 | Fulham | H | L | 0-1 | 17337 | |
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| Tue 22nd Feb | --:-- | FL1 | Bolton Wanderers | A | L | 0-3 | 12672 | |
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| Wed 1st Mar | --:-- | FL1 | Tranmere Rovers | H | L | 1-2 | 10759 | |
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| Sat 4th Mar | --:-- | FL1 | Ipswich Town | A | W | 1-0 | 20305 | |
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| Tue 7th Mar | --:-- | FL1 | Birmingham City | A | L | 0-1 | 19573 | |
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| Sat 11th Mar | --:-- | FL1 | Nottingham Forest | H | W | 2-1 | 14336 | |
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| Sat 18th Mar | --:-- | FL1 | Crewe Alexandra | A | W | 3-1 | 6188 | |
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| Tue 21st Mar | --:-- | FL1 | West Bromwich Albion | H | W | 2-0 | 14760 | |
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| Sat 25th Mar | --:-- | FL1 | Swindon Town | H | W | 4-1 | 15305 | |
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| Sat 1st Apr | --:-- | FL1 | Port Vale | A | L | 0-2 | 5426 | |
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| Sat 8th Apr | --:-- | FL1 | Norwich City | H | W | 2-1 | 14003 | |
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| Sat 15th Apr | --:-- | FL1 | Blackburn Rovers | A | D | 1-1 | 17263 | |
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| Fri 21st Apr | --:-- | FL1 | Charlton Athletic | A | D | 1-1 | 20043 | |
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| Mon 24th Apr | --:-- | FL1 | Manchester City | H | D | 2-2 | 19015 | |
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| Sat 29th Apr | --:-- | FL1 | Walsall | A | L | 0-1 | 8151 | |
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| Sun 7th May | --:-- | FL1 | Queens Park Rangers | H | L | 1-3 | 16301 | |