Southend United
1998-1999
[squad stats] [appearance chart]
| Date | K.O. | Comp | Opponents | Ven | Res | Att | ||||
| Sat 8th Aug | --:-- | FL3 | Scarborough | A | W | 2-1 |  |
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| Tue 11th Aug | --:-- | LC | Gillingham | H | W | 1-0 | |
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| Sat 15th Aug | --:-- | FL3 | Shrewsbury Town | H | W | 2-1 | |
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| Tue 18th Aug | --:-- | LC | Gillingham | A | W | 1-0 | |
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| Sat 22nd Aug | --:-- | FL3 | Peterborough United | A | D | 1-1 | |
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| Sat 29th Aug | --:-- | FL3 | Chester City | H | L | 0-1 | |
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| Tue 1st Sep | --:-- | FL3 | Carlisle United | A | L | 0-3 | |
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| Sat 5th Sep | --:-- | FL3 | Rotherham United | H | W | 3-0 | |
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| Tue 8th Sep | --:-- | FL3 | Halifax Town | H | D | 0-0 | |
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| Sat 12th Sep | --:-- | FL3 | Brighton and Hove Albion | A | W | 2-0 | |
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| Wed 16th Sep | --:-- | LC | Coventry City | A | L | 0-1 | |
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| Sat 19th Sep | --:-- | FL3 | Cambridge United | H | L | 0-1 | 5009 |  |
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| Tue 22nd Sep | --:-- | LC | Coventry City | H | L | 0-4 | |
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| Sat 26th Sep | --:-- | FL3 | Swansea City | A | L | 1-3 | |
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| Sat 3rd Oct | --:-- | FL3 | Rochdale | H | D | 1-1 | |
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| Sat 10th Oct | --:-- | FL3 | Scunthorpe United | A | D | 1-1 | |
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| Sat 17th Oct | --:-- | FL3 | Leyton Orient | H | D | 2-2 | |
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| Tue 20th Oct | --:-- | FL3 | Mansfield Town | H | L | 1-2 | |
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| Sat 24th Oct | --:-- | FL3 | Hull City | A | D | 1-1 | |
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| Sat 31st Oct | --:-- | FL3 | Darlington | H | W | 2-1 | |
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| Sat 7th Nov | --:-- | FL3 | Exeter City | A | L | 1-2 | |
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| Tue 10th Nov | --:-- | FL3 | Brentford | A | L | 1-4 | |
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| Sat 14th Nov | --:-- | FAC | Doncaster Rovers | H | L | 0-1 | |
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| Sat 21st Nov | --:-- | FL3 | Plymouth Argyle | H | W | 1-0 | |
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| Sat 28th Nov | --:-- | FL3 | Cardiff City | A | L | 0-2 | |
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| Sat 12th Dec | --:-- | FL3 | Barnet | H | L | 2-3 | |
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| Sat 19th Dec | --:-- | FL3 | Hartlepool United | A | W | 4-2 | |
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| Sat 26th Dec | --:-- | FL3 | Peterborough United | H | W | 2-0 | |
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| Mon 28th Dec | --:-- | FL3 | Torquay United | A | L | 0-2 | |
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| Sat 2nd Jan | --:-- | FL3 | Chester City | A | D | 1-1 | |
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| Tue 5th Jan | --:-- | AMC | Exeter City | A | L | 1-3 | |
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| Sat 9th Jan | --:-- | FL3 | Scarborough | H | W | 1-0 | |
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| Sat 16th Jan | --:-- | FL3 | Shrewsbury Town | A | L | 1-3 | |
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| Sat 23rd Jan | --:-- | FL3 | Carlisle United | H | L | 0-1 | |
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| Sat 30th Jan | --:-- | FL3 | Torquay United | H | D | 0-0 | |
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| Sat 6th Feb | --:-- | FL3 | Rotherham United | A | D | 2-2 | |
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| Sat 13th Feb | --:-- | FL3 | Halifax Town | A | L | 1-3 | |
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| Sat 20th Feb | --:-- | FL3 | Brighton and Hove Albion | H | W | 3-0 | |
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| Sat 27th Feb | --:-- | FL3 | Cambridge United | A | L | 0-3 | 5013 | |
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| Sat 6th Mar | --:-- | FL3 | Swansea City | H | W | 2-0 | |
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| Sat 13th Mar | --:-- | FL3 | Exeter City | H | D | 0-0 | |
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| Sat 20th Mar | --:-- | FL3 | Darlington | A | L | 1-2 | |
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| Fri 26th Mar | --:-- | FL3 | Hull City | H | L | 0-1 | |
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| Tue 30th Mar | --:-- | FL3 | Rochdale | A | L | 0-1 | |
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| Sat 3rd Apr | --:-- | FL3 | Leyton Orient | A | W | 3-0 | |
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| Mon 5th Apr | --:-- | FL3 | Scunthorpe United | H | L | 0-1 | |
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| Sat 10th Apr | --:-- | FL3 | Mansfield Town | A | D | 0-0 | |
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| Tue 13th Apr | --:-- | FL3 | Cardiff City | H | L | 0-1 | |
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| Sat 17th Apr | --:-- | FL3 | Plymouth Argyle | A | W | 3-0 | |
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| Sat 24th Apr | --:-- | FL3 | Brentford | H | L | 1-4 | |
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| Sat 1st May | --:-- | FL3 | Barnet | A | W | 2-0 | |
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| Sat 8th May | --:-- | FL3 | Hartlepool United | H | D | 1-1 | |