Hartlepool United
1999-2000
[squad stats] [appearance chart]
| Date | K.O. | Comp | Opponents | Ven | Res | Att | ||||
| Sat 7th Aug | --:-- | FL3 | Peterborough United | A | L | 1-2 | 5886 |  |
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| Tue 10th Aug | --:-- | LC | Crewe Alexandra | H | D | 3-3 | |
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| Sat 14th Aug | --:-- | FL3 | Halifax Town | H | L | 0-2 | 2719 | |
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| Sat 21st Aug | --:-- | FL3 | Carlisle United | A | W | 3-0 | 4033 | |
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| Tue 24th Aug | --:-- | LC | Crewe Alexandra | A | L | 0-1 | |
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| Sat 28th Aug | --:-- | FL3 | Cheltenham Town | H | L | 0-1 | 2390 | |
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| Tue 31st Aug | --:-- | FL3 | Shrewsbury Town | A | D | 0-0 | 1803 | |
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| Sat 4th Sep | --:-- | FL3 | Southend United | H | L | 1-2 | 1980 | |
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| Sat 11th Sep | --:-- | FL3 | Northampton Town | A | L | 1-2 | 4724 | |
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| Sat 18th Sep | --:-- | FL3 | Plymouth Argyle | H | W | 3-0 | 2242 | |
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| Sat 25th Sep | --:-- | FL3 | Leyton Orient | A | L | 1-2 | 3889 | |
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| Sat 2nd Oct | --:-- | FL3 | Darlington | H | W | 2-0 | 3957 | |
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| Sat 9th Oct | --:-- | FL3 | Hull City | H | W | 2-0 | 3114 | |
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| Sat 16th Oct | --:-- | FL3 | Mansfield Town | A | W | 3-2 | 2612 | |
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| Tue 19th Oct | --:-- | FL3 | Rotherham United | A | L | 0-3 | 3340 | |
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| Sat 23rd Oct | --:-- | FL3 | Leyton Orient | H | W | 1-0 | 2397 | |
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| Sun 31st Oct | --:-- | FAC | Millwall | H | W | 1-0 | |
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| Tue 2nd Nov | --:-- | FL3 | Barnet | H | W | 3-0 | 2290 | |
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| Sat 6th Nov | --:-- | FL3 | Brighton and Hove Albion | A | L | 0-1 | 5746 | |
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| Sat 13th Nov | --:-- | FL3 | Chester City | H | W | 1-0 | 2266 | |
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| Sun 21st Nov | --:-- | FAC | Hereford United | A | L | 0-1 | |
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| Tue 23rd Nov | --:-- | FL3 | Torquay United | A | D | 0-0 | 2080 | |
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| Sat 27th Nov | --:-- | FL3 | Macclesfield Town | A | D | 3-3 | 2351 | |
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| Sat 4th Dec | --:-- | FL3 | Peterborough United | H | W | 1-0 | 2404 | |
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| Tue 7th Dec | --:-- | AMC | Halifax Town | H | W | 1-0 | |
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| Sat 11th Dec | --:-- | FL3 | Swansea City | H | L | 0-1 | 2397 | |
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| Sat 18th Dec | --:-- | FL3 | Exeter City | A | W | 2-1 | 2261 | |
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| Sun 26th Dec | --:-- | FL3 | York City | H | W | 2-1 | 4668 | |
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| Tue 28th Dec | --:-- | FL3 | Lincoln City | A | W | 2-1 | 3480 | |
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| Mon 3rd Jan | --:-- | FL3 | Rochdale | H | W | 3-2 | 4498 | |
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| Sat 8th Jan | --:-- | FL3 | Swansea City | A | L | 1-2 | 7163 | |
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| Mon 10th Jan | --:-- | AMC | Preston North End | A | W | 2-1 | |
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| Sat 15th Jan | --:-- | FL3 | Halifax Town | A | D | 1-1 | 3546 | |
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| Sat 22nd Jan | --:-- | FL3 | Carlisle United | H | W | 1-0 | 3530 | |
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| Sat 29th Jan | --:-- | FL3 | Cheltenham Town | A | L | 1-2 | 3630 | |
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| Sat 5th Feb | --:-- | FL3 | Shrewsbury Town | H | W | 1-0 | 2933 | |
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| Sat 12th Feb | --:-- | FL3 | Southend United | A | L | 1-2 | 3337 | |
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| Sat 19th Feb | --:-- | FL3 | Macclesfield Town | H | L | 1-4 | 2823 | |
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| Tue 22nd Feb | --:-- | AMC | Carlisle United | H | L | 1-2 | |
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| Sat 26th Feb | --:-- | FL3 | Plymouth Argyle | A | D | 1-1 | 3917 | |
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| Sat 4th Mar | --:-- | FL3 | Northampton Town | H | W | 2-1 | 2878 | |
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| Tue 7th Mar | --:-- | FL3 | Brighton and Hove Albion | H | D | 0-0 | 2734 | |
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| Sat 11th Mar | --:-- | FL3 | Barnet | A | D | 1-1 | 2925 | |
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| Sat 18th Mar | --:-- | FL3 | Torquay United | H | W | 2-0 | 2766 | |
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| Tue 21st Mar | --:-- | FL3 | Chester City | A | D | 1-1 | 1816 | |
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| Sat 25th Mar | --:-- | FL3 | York City | A | L | 1-2 | 4079 | |
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| Sat 1st Apr | --:-- | FL3 | Exeter City | H | W | 2-1 | 2668 | |
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| Sat 8th Apr | --:-- | FL3 | Rochdale | A | L | 0-2 | 2332 | |
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| Sat 15th Apr | --:-- | FL3 | Lincoln City | H | W | 2-0 | 2777 | |
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| Sat 22nd Apr | --:-- | FL3 | Mansfield Town | H | W | 1-0 | 3473 | |
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| Mon 24th Apr | --:-- | FL3 | Darlington | A | D | 1-1 | 6746 | |
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| Sat 29th Apr | --:-- | FL3 | Rotherham United | H | L | 1-2 | 4673 | |
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| Sat 6th May | --:-- | FL3 | Hull City | A | W | 3-0 | 7620 | |
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| Sat 13th May | 15:00 | FL3 P/O | Darlington | H | L | 0-2 | 6995 | |
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| Wed 17th May | 19:45 | FL3 P/O | Darlington | A | L | 0-1 | 8238 | |