Chesterfield
1999-2000
[squad stats] [appearance chart]
| Date | K.O. | Comp | Opponents | Ven | Res | Att | ||||
| Sat 7th Aug | --:-- | FL2 | Colchester United | H | L | 0-1 | 2930 |  |
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| Tue 10th Aug | --:-- | LC | Rochdale | A | W | 2-1 | |
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| Sat 14th Aug | --:-- | FL2 | Burnley | A | L | 1-2 | 10615 | |
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| Sat 21st Aug | --:-- | FL2 | Cambridge United | H | W | 4-2 | 2816 |  |
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| Tue 24th Aug | --:-- | LC | Rochdale | H | W | 2-1 | |
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| Sat 28th Aug | --:-- | FL2 | Millwall | A | D | 1-1 | 6256 | |
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| Sat 4th Sep | --:-- | FL2 | Preston North End | A | W | 2-0 | 8506 | |
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| Sat 11th Sep | --:-- | FL2 | Stoke City | H | L | 0-2 | 4285 | |
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| Tue 14th Sep | --:-- | LC | Middlesbrough | H | D | 0-0 | |
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| Sat 18th Sep | --:-- | FL2 | Reading | A | L | 0-1 | 6932 | |
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| Tue 21st Sep | --:-- | LC | Middlesbrough | A | L | 1-2 | |
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| Sat 25th Sep | --:-- | FL2 | Scunthorpe United | A | D | 0-0 | 4321 | |
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| Sat 2nd Oct | --:-- | FL2 | AFC Bournemouth | H | L | 0-1 | 2775 | |
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| Sat 9th Oct | --:-- | FL2 | Blackpool | H | D | 0-0 | 2804 | |
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| Sat 16th Oct | --:-- | FL2 | Wrexham | A | D | 1-1 | 2603 | |
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| Tue 19th Oct | --:-- | FL2 | Notts County | A | L | 0-1 | 4749 | |
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| Sat 23rd Oct | --:-- | FL2 | Scunthorpe United | H | D | 1-1 | 3464 | |
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| Sat 30th Oct | --:-- | FAC | Enfield | H | L | 1-2 | |
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| Tue 2nd Nov | --:-- | FL2 | Wigan Athletic | A | L | 0-3 | 4376 | |
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| Sat 6th Nov | --:-- | FL2 | Oldham Athletic | H | L | 0-1 | 2737 | |
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| Fri 12th Nov | --:-- | FL2 | Cardiff City | A | L | 1-2 | 4863 | |
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| Sat 20th Nov | --:-- | FL2 | Bristol Rovers | H | L | 0-1 | 2875 | |
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| Sat 27th Nov | --:-- | FL2 | Oxford United | H | D | 0-0 | 2768 | |
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| Fri 3rd Dec | --:-- | FL2 | Colchester United | A | L | 0-1 | 3027 | |
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| Tue 7th Dec | --:-- | FL2 | Bristol City | H | L | 0-2 | 2254 | |
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| Fri 10th Dec | --:-- | FL2 | Brentford | A | D | 1-1 | 4286 | |
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| Sun 26th Dec | --:-- | FL2 | Luton Town | A | D | 1-1 | 5870 | |
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| Mon 3rd Jan | --:-- | FL2 | Wycombe Wanderers | A | L | 0-3 | 5001 | |
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| Sat 8th Jan | --:-- | FL2 | Brentford | H | W | 1-0 | 2746 | |
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| Tue 11th Jan | --:-- | AMC | Rotherham United | A | W | 4-1 | |
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| Sat 15th Jan | --:-- | FL2 | Burnley | H | D | 1-1 | 4214 | |
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| Sat 22nd Jan | --:-- | FL2 | Cambridge United | A | L | 0-2 | 3819 | |
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| Tue 25th Jan | --:-- | AMC | Scunthorpe United | A | W | 2-1 | |
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| Sat 29th Jan | --:-- | FL2 | Millwall | H | W | 2-0 | 3198 | |
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| Tue 1st Feb | --:-- | FL2 | Gillingham | H | D | 0-0 | 2898 | |
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| Sat 5th Feb | --:-- | FL2 | Bristol City | A | L | 0-3 | 8837 | |
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| Sat 12th Feb | --:-- | FL2 | Preston North End | H | L | 0-1 | 4726 | |
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| Tue 15th Feb | --:-- | AMC | Stoke City | H | L | 0-1 | |
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| Sat 19th Feb | --:-- | FL2 | Oxford United | A | L | 1-2 | 5146 | |
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| Sat 26th Feb | --:-- | FL2 | Reading | H | W | 2-0 | 2986 | |
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| Sat 4th Mar | --:-- | FL2 | Stoke City | A | L | 1-5 | 11968 | |
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| Sat 11th Mar | --:-- | FL2 | Wigan Athletic | H | D | 1-1 | 3106 | |
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| Sat 18th Mar | --:-- | FL2 | Bristol Rovers | A | L | 1-3 | 8765 | |
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| Tue 21st Mar | --:-- | FL2 | Cardiff City | H | D | 1-1 | 2348 | |
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| Sat 25th Mar | --:-- | FL2 | Luton Town | H | L | 1-3 | 2597 | |
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| Tue 28th Mar | --:-- | FL2 | Bury | H | L | 0-1 | 1903 | |
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| Sat 1st Apr | --:-- | FL2 | Gillingham | A | L | 0-1 | 6772 | |
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| Sat 8th Apr | --:-- | FL2 | Wycombe Wanderers | H | L | 1-2 | 2081 | |
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| Sat 15th Apr | --:-- | FL2 | Bury | A | D | 1-1 | 3021 | |
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| Tue 18th Apr | --:-- | FL2 | Oldham Athletic | A | W | 2-1 | 4012 | |
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| Sat 22nd Apr | --:-- | FL2 | Wrexham | H | L | 0-3 | 2550 | |
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| Tue 25th Apr | --:-- | FL2 | AFC Bournemouth | A | D | 1-1 | 3481 | |
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| Sat 29th Apr | --:-- | FL2 | Notts County | H | W | 2-1 | 2455 | |
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| Sat 6th May | --:-- | FL2 | Blackpool | A | D | 2-2 | 3860 | |