Southend United
1999-2000
[squad stats] [appearance chart]
| Date | K.O. | Comp | Opponents | Ven | Res | Att | ||||
| Sat 7th Aug | --:-- | FL3 | Plymouth Argyle | H | W | 2-1 | 4981 |  |
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| Tue 10th Aug | --:-- | LC | Oxford United | H | L | 0-2 | |
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| Sat 14th Aug | --:-- | FL3 | Rochdale | A | L | 0-2 | 2253 | |
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| Sat 21st Aug | --:-- | FL3 | Mansfield Town | H | W | 1-0 | 3533 | |
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| Tue 24th Aug | --:-- | LC | Oxford United | A | L | 0-1 | |
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| Sat 28th Aug | --:-- | FL3 | Swansea City | A | L | 1-3 | 4757 | |
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| Mon 30th Aug | --:-- | FL3 | Leyton Orient | H | D | 1-1 | 5980 | |
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| Sat 4th Sep | --:-- | FL3 | Hartlepool United | A | W | 2-1 | 1980 | |
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| Sat 11th Sep | --:-- | FL3 | Macclesfield Town | A | W | 2-1 | 2059 | |
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| Sat 18th Sep | --:-- | FL3 | Halifax Town | H | W | 4-1 | 4533 | |
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| Sat 25th Sep | --:-- | FL3 | Peterborough United | H | L | 0-1 | 6187 | |
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| Sat 2nd Oct | --:-- | FL3 | Carlisle United | A | D | 1-1 | 2800 | |
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| Sat 9th Oct | --:-- | FL3 | Cheltenham Town | A | L | 1-2 | 3118 | |
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| Sat 16th Oct | --:-- | FL3 | Shrewsbury Town | H | W | 3-2 | 3963 | |
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| Tue 19th Oct | --:-- | FL3 | Lincoln City | H | D | 2-2 | 3556 | |
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| Sat 23rd Oct | --:-- | FL3 | Peterborough United | A | L | 0-1 | 5860 | |
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| Sat 30th Oct | --:-- | FAC | Torquay United | A | L | 0-1 | |
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| Tue 2nd Nov | --:-- | FL3 | Brighton and Hove Albion | H | W | 2-1 | 4927 | |
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| Sat 6th Nov | --:-- | FL3 | Exeter City | A | W | 1-0 | 2353 | |
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| Fri 12th Nov | --:-- | FL3 | Hull City | H | L | 1-2 | 4940 | |
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| Tue 23rd Nov | --:-- | FL3 | Chester City | A | D | 0-0 | 1906 | |
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| Sat 27th Nov | --:-- | FL3 | Darlington | H | L | 1-2 | 4134 | |
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| Sat 4th Dec | --:-- | FL3 | Plymouth Argyle | A | L | 1-3 | 4679 | |
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| Tue 7th Dec | --:-- | AMC | Cheltenham Town | H | L | 0-1 | |
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| Fri 10th Dec | --:-- | FL3 | Barnet | H | L | 1-3 | 3521 | |
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| Fri 17th Dec | --:-- | FL3 | York City | A | D | 2-2 | 2233 | |
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| Sun 26th Dec | --:-- | FL3 | Northampton Town | H | D | 2-2 | 5449 | |
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| Tue 28th Dec | --:-- | FL3 | Torquay United | A | W | 1-0 | 3138 | |
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| Mon 3rd Jan | --:-- | FL3 | Rotherham United | H | L | 1-2 | 4788 | |
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| Sat 8th Jan | --:-- | FL3 | Barnet | A | L | 1-2 | 3057 | |
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| Sat 15th Jan | --:-- | FL3 | Rochdale | H | D | 3-3 | 3190 | |
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| Sat 22nd Jan | --:-- | FL3 | Mansfield Town | A | L | 1-3 | 2215 | |
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| Sat 29th Jan | --:-- | FL3 | Swansea City | H | W | 2-1 | 3860 | |
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| Sat 5th Feb | --:-- | FL3 | Leyton Orient | A | L | 1-2 | 5972 | |
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| Sat 12th Feb | --:-- | FL3 | Hartlepool United | H | W | 2-1 | 3337 | |
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| Sat 19th Feb | --:-- | FL3 | Darlington | A | L | 0-1 | 4391 | |
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| Sat 26th Feb | --:-- | FL3 | Halifax Town | A | D | 0-0 | 2068 | |
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| Fri 3rd Mar | --:-- | FL3 | Macclesfield Town | H | W | 1-0 | 3725 | |
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| Tue 7th Mar | --:-- | FL3 | Exeter City | H | L | 1-2 | 3122 | |
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| Sat 11th Mar | --:-- | FL3 | Brighton and Hove Albion | A | L | 0-1 | 5844 | |
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| Sat 18th Mar | --:-- | FL3 | Chester City | H | W | 3-1 | 3483 | |
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| Tue 21st Mar | --:-- | FL3 | Hull City | A | D | 0-0 | 4150 | |
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| Sat 25th Mar | --:-- | FL3 | Northampton Town | A | L | 0-2 | 5426 | |
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| Sat 1st Apr | --:-- | FL3 | York City | H | D | 0-0 | 3364 | |
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| Sat 8th Apr | --:-- | FL3 | Rotherham United | A | D | 0-0 | 4327 | |
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| Sat 22nd Apr | --:-- | FL3 | Shrewsbury Town | A | L | 1-2 | 3540 | |
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| Mon 24th Apr | --:-- | FL3 | Carlisle United | H | W | 2-0 | 3053 | |
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| Sat 29th Apr | --:-- | FL3 | Lincoln City | A | L | 0-1 | 2556 | |
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| Tue 2nd May | --:-- | FL3 | Torquay United | H | L | 0-2 | 2563 | |
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| Sat 6th May | --:-- | FL3 | Cheltenham Town | H | W | 2-1 | 4977 | |