Chesterfield
1998-1999
[squad stats] [appearance chart]
| Date | K.O. | Comp | Opponents | Ven | Res | Att | ||||
| Sat 8th Aug | --:-- | FL2 | Colchester United | A | L | 0-1 |  |
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| Tue 11th Aug | --:-- | LC | Rotherham United | A | W | 1-0 | |
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| Sat 15th Aug | --:-- | FL2 | Burnley | H | W | 1-0 | |
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| Tue 18th Aug | --:-- | LC | Rotherham United | H | W | 2-0 | |
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| Sat 22nd Aug | --:-- | FL2 | Oldham Athletic | A | L | 0-2 | |
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| Sat 29th Aug | --:-- | FL2 | Reading | H | W | 1-0 | |
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| Mon 31st Aug | --:-- | FL2 | Preston North End | A | L | 0-2 | |
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| Sat 5th Sep | --:-- | FL2 | Gillingham | H | W | 1-0 | |
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| Tue 8th Sep | --:-- | FL2 | Bristol Rovers | A | D | 0-0 | |
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| Sat 12th Sep | --:-- | FL2 | Walsall | H | L | 0-1 | |
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| Wed 16th Sep | --:-- | LC | Leicester City | A | L | 0-3 | |
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| Sat 19th Sep | --:-- | FL2 | Manchester City | A | D | 1-1 | |
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| Tue 22nd Sep | --:-- | LC | Leicester City | H | L | 1-3 | |
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| Sat 26th Sep | --:-- | FL2 | Wrexham | H | W | 2-1 | |
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| Sat 3rd Oct | --:-- | FL2 | Millwall | A | D | 0-0 | |
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| Mon 12th Oct | --:-- | FL2 | Stoke City | A | D | 0-0 | |
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| Sat 17th Oct | --:-- | FL2 | York City | H | W | 2-1 | |
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| Tue 20th Oct | --:-- | FL2 | Notts County | H | W | 3-0 | |
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| Sat 7th Nov | --:-- | FL2 | Lincoln City | H | W | 3-0 | |
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| Tue 10th Nov | --:-- | FL2 | AFC Bournemouth | H | W | 3-1 | |
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| Sat 14th Nov | --:-- | FAC | Wycombe Wanderers | A | L | 0-1 | |
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| Sat 21st Nov | --:-- | FL2 | Fulham | A | L | 1-2 | |
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| Sat 28th Nov | --:-- | FL2 | Macclesfield Town | H | W | 2-0 | |
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| Sat 5th Dec | --:-- | FL2 | Blackpool | A | D | 1-1 | |
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| Sat 12th Dec | --:-- | FL2 | Northampton Town | A | L | 0-1 | |
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| Sat 19th Dec | --:-- | FL2 | Wigan Athletic | H | D | 1-1 | |
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| Sat 26th Dec | --:-- | FL2 | Oldham Athletic | H | L | 1-3 | |
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| Mon 28th Dec | --:-- | FL2 | Wycombe Wanderers | A | L | 0-1 | |
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| Sat 2nd Jan | --:-- | FL2 | Reading | A | W | 2-1 | |
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| Sat 9th Jan | --:-- | FL2 | Colchester United | H | W | 3-1 | |
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| Tue 12th Jan | --:-- | AMC | Darlington | A | W | 2-0 | |
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| Sat 16th Jan | --:-- | FL2 | Burnley | A | W | 2-1 | |
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| Tue 19th Jan | --:-- | AMC | Wrexham | A | L | 2-3 | |
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| Sat 23rd Jan | --:-- | FL2 | Preston North End | H | L | 0-1 | |
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| Sat 30th Jan | --:-- | FL2 | Wycombe Wanderers | H | W | 2-0 | |
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| Sat 6th Feb | --:-- | FL2 | Gillingham | A | L | 1-3 | |
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| Sat 20th Feb | --:-- | FL2 | Walsall | A | D | 1-1 | |
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| Sat 27th Feb | --:-- | FL2 | Manchester City | H | D | 1-1 | |
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| Tue 2nd Mar | --:-- | FL2 | Millwall | H | W | 2-1 | |
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| Sat 6th Mar | --:-- | FL2 | Wrexham | A | D | 0-0 | |
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| Sat 13th Mar | --:-- | FL2 | Lincoln City | A | L | 0-2 | |
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| Sat 20th Mar | --:-- | FL2 | Luton Town | H | W | 3-1 | |
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| Sat 27th Mar | --:-- | FL2 | Blackpool | H | L | 1-2 | |
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| Sat 3rd Apr | --:-- | FL2 | York City | A | W | 2-1 | |
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| Mon 5th Apr | --:-- | FL2 | Stoke City | H | D | 1-1 | |
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| Sat 10th Apr | --:-- | FL2 | Notts County | A | L | 0-2 | |
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| Tue 13th Apr | --:-- | FL2 | Macclesfield Town | A | L | 0-2 | |
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| Sat 17th Apr | --:-- | FL2 | Fulham | H | W | 1-0 | |
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| Tue 20th Apr | --:-- | FL2 | Bristol Rovers | H | D | 0-0 | |
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| Sat 24th Apr | --:-- | FL2 | AFC Bournemouth | A | D | 0-0 | |
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| Tue 27th Apr | --:-- | FL2 | Luton Town | A | L | 0-1 | |
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| Mon 3rd May | --:-- | FL2 | Northampton Town | H | D | 0-0 | |
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| Sat 8th May | --:-- | FL2 | Wigan Athletic | A | L | 1-3 | |