Gillingham
1999-2000
[squad stats] [appearance chart]
| Date | K.O. | Comp | Opponents | Ven | Res | Att | ||||
| Sat 7th Aug | --:-- | FL2 | Bury | A | L | 1-2 | 4014 |  |
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| Wed 11th Aug | --:-- | LC | Brighton and Hove Albion | A | W | 2-0 | |
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| Sat 14th Aug | --:-- | FL2 | Bristol Rovers | H | L | 0-1 | 6234 | |
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| Sat 21st Aug | --:-- | FL2 | Blackpool | A | D | 1-1 | 4203 | |
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| Tue 24th Aug | --:-- | LC | Brighton and Hove Albion | H | W | 2-0 | |
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| Sat 28th Aug | --:-- | FL2 | Wycombe Wanderers | H | D | 2-2 | 6180 | |
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| Mon 30th Aug | --:-- | FL2 | Stoke City | A | D | 1-1 | 8369 | |
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| Sat 4th Sep | --:-- | FL2 | Oldham Athletic | H | W | 2-1 | 5884 | |
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| Sat 11th Sep | --:-- | FL2 | Oxford United | A | W | 2-1 | 5418 | |
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| Tue 14th Sep | --:-- | LC | Bolton Wanderers | H | L | 1-4 | |
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| Sat 18th Sep | --:-- | FL2 | Preston North End | H | L | 0-2 | 6610 | |
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| Tue 21st Sep | --:-- | LC | Bolton Wanderers | A | L | 0-2 | |
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| Sat 25th Sep | --:-- | FL2 | Cambridge United | A | D | 2-2 | 4708 |  |
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| Sat 2nd Oct | --:-- | FL2 | Millwall | H | W | 2-0 | 6616 | |
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| Sat 9th Oct | --:-- | FL2 | Wrexham | H | W | 5-1 | 5997 | |
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| Sat 16th Oct | --:-- | FL2 | Luton Town | A | L | 1-3 | 6394 | |
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| Tue 19th Oct | --:-- | FL2 | Brentford | A | W | 2-1 | 6264 | |
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| Sat 23rd Oct | --:-- | FL2 | Cambridge United | H | W | 2-1 | 6417 | |
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| Sat 30th Oct | --:-- | FAC | Cheltenham Town | A | D | 1-1 | |
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| Tue 2nd Nov | --:-- | FL2 | Bristol City | H | W | 3-0 | 6892 | |
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| Sat 6th Nov | --:-- | FL2 | Notts County | A | D | 1-1 | 6023 | |
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| Tue 9th Nov | --:-- | FAC | Cheltenham Town | H | W | 3-2 | |
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| Fri 12th Nov | --:-- | FL2 | AFC Bournemouth | H | W | 4-1 | 6336 | |
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| Sat 20th Nov | --:-- | FAC | Darlington | H | W | 3-1 | |
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| Tue 23rd Nov | --:-- | FL2 | Scunthorpe United | A | W | 4-1 | 3444 | |
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| Sat 27th Nov | --:-- | FL2 | Cardiff City | A | W | 2-1 | 7608 | |
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| Sat 4th Dec | --:-- | FL2 | Bury | H | W | 1-0 | 7036 | |
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| Tue 7th Dec | --:-- | AMC | Torquay United | H | L | 0-3 | |
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| Sat 11th Dec | --:-- | FAC | Walsall | A | D | 1-1 | |
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| Sun 26th Dec | --:-- | FL2 | Colchester United | H | W | 2-1 | 7338 | |
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| Tue 28th Dec | --:-- | FL2 | Wigan Athletic | A | L | 0-2 | 8054 | |
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| Mon 3rd Jan | --:-- | FL2 | Reading | H | D | 2-2 | 7453 | |
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| Sat 8th Jan | --:-- | FAC | Walsall | H | W | 2-1 | |
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| Tue 11th Jan | --:-- | FAC | Bradford City | H | W | 3-1 | |
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| Sat 15th Jan | --:-- | FL2 | Bristol Rovers | A | L | 1-2 | 8331 | |
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| Sat 22nd Jan | --:-- | FL2 | Blackpool | H | L | 1-3 | 6805 | |
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| Sat 29th Jan | --:-- | FAC | Sheffield Wednesday | H | W | 3-1 | |
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| Tue 1st Feb | --:-- | FL2 | Chesterfield | A | D | 0-0 | 2898 | |
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| Sat 5th Feb | --:-- | FL2 | Stoke City | H | W | 3-0 | 7801 | |
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| Sat 12th Feb | --:-- | FL2 | Oldham Athletic | A | W | 3-1 | 5144 | |
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| Sun 20th Feb | --:-- | FAC | Chelsea | A | L | 0-5 | |
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| Sat 26th Feb | --:-- | FL2 | Preston North End | A | W | 2-0 | 13246 | |
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| Sat 4th Mar | --:-- | FL2 | Oxford United | H | W | 1-0 | 6966 | |
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| Tue 7th Mar | --:-- | FL2 | Notts County | H | L | 0-1 | 6915 | |
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| Sat 11th Mar | --:-- | FL2 | Bristol City | A | W | 1-0 | 9332 | |
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| Tue 14th Mar | --:-- | FL2 | Burnley | H | D | 2-2 | 7347 | |
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| Sat 18th Mar | --:-- | FL2 | Scunthorpe United | H | W | 3-1 | 6822 | |
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| Tue 21st Mar | --:-- | FL2 | AFC Bournemouth | A | W | 1-0 | 4443 | |
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| Sat 25th Mar | --:-- | FL2 | Colchester United | A | L | 1-2 | 4337 | |
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| Tue 28th Mar | --:-- | FL2 | Wycombe Wanderers | A | L | 0-1 | 4183 | |
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| Sat 1st Apr | --:-- | FL2 | Chesterfield | H | W | 1-0 | 6772 | |
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| Fri 7th Apr | --:-- | FL2 | Reading | A | D | 2-2 | 11064 | |
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| Sat 15th Apr | --:-- | FL2 | Wigan Athletic | H | W | 2-1 | 7746 | |
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| Tue 18th Apr | --:-- | FL2 | Burnley | A | W | 3-0 | 17026 | |
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| Sat 22nd Apr | --:-- | FL2 | Luton Town | H | W | 2-0 | 8667 | |
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| Mon 24th Apr | --:-- | FL2 | Millwall | A | D | 2-2 | 17929 | |
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| Sat 29th Apr | --:-- | FL2 | Brentford | H | W | 2-0 | 9001 | |
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| Tue 2nd May | --:-- | FL2 | Cardiff City | H | W | 4-1 | 9178 | |
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| Sat 6th May | --:-- | FL2 | Wrexham | A | L | 0-1 | 8811 | |
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| Sat 13th May | 15:00 | FL2 P/O | Stoke City | A | L | 2-3 | 22124 | |
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| Wed 17th May | 19:45 | FL2 P/O | Stoke City | H | W | 3-0 | 10386 | |
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| Sun 28th May | 15:00 | FL2 P/O | Wigan Athletic | - | W | 3-2 | 53764 | |