Gillingham
1998-1999
[squad stats] [appearance chart]
| Date | K.O. | Comp | Opponents | Ven | Res | Att | ||||
| Sat 8th Aug | --:-- | FL2 | Walsall | H | L | 0-1 |  |
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| Tue 11th Aug | --:-- | LC | Southend United | A | L | 0-1 | |
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| Sat 15th Aug | --:-- | FL2 | York City | A | D | 1-1 | |
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| Tue 18th Aug | --:-- | LC | Southend United | H | L | 0-1 | |
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| Sat 22nd Aug | --:-- | FL2 | Bristol Rovers | H | D | 0-0 | |
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| Sat 29th Aug | --:-- | FL2 | Blackpool | A | D | 2-2 | |
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| Tue 1st Sep | --:-- | FL2 | Wrexham | H | W | 4-0 | |
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| Sat 5th Sep | --:-- | FL2 | Chesterfield | A | L | 0-1 | |
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| Tue 8th Sep | --:-- | FL2 | Northampton Town | H | L | 2-3 | |
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| Sat 12th Sep | --:-- | FL2 | Colchester United | A | D | 1-1 | |
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| Sat 19th Sep | --:-- | FL2 | Burnley | H | W | 2-1 | |
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| Sat 26th Sep | --:-- | FL2 | Preston North End | A | D | 1-1 | |
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| Sat 3rd Oct | --:-- | FL2 | Macclesfield Town | H | D | 2-2 | |
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| Sat 10th Oct | --:-- | FL2 | Wycombe Wanderers | H | W | 3-0 | |
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| Sat 17th Oct | --:-- | FL2 | Reading | A | D | 0-0 | |
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| Tue 20th Oct | --:-- | FL2 | AFC Bournemouth | A | D | 3-3 | |
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| Sat 24th Oct | --:-- | FL2 | Luton Town | H | W | 1-0 | |
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| Sat 31st Oct | --:-- | FL2 | Lincoln City | A | W | 2-1 | |
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| Sat 7th Nov | --:-- | FL2 | Wigan Athletic | H | W | 2-0 | |
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| Tue 10th Nov | --:-- | FL2 | Oldham Athletic | H | W | 2-1 | |
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| Sat 14th Nov | --:-- | FAC | Oldham Athletic | A | L | 0-2 | |
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| Sat 21st Nov | --:-- | FL2 | Manchester City | A | D | 0-0 | |
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| Sat 28th Nov | --:-- | FL2 | Fulham | H | W | 1-0 | |
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| Sat 5th Dec | --:-- | AMC | Colchester United | A | W | 5-1 | |
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| Sat 12th Dec | --:-- | FL2 | Stoke City | A | D | 0-0 | |
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| Sat 19th Dec | --:-- | FL2 | Notts County | H | W | 4-0 | |
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| Tue 29th Dec | --:-- | FL2 | Millwall | H | D | 1-1 | |
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| Sat 2nd Jan | --:-- | FL2 | Blackpool | H | W | 1-0 | |
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| Tue 5th Jan | --:-- | AMC | Swansea City | A | W | 1-0 | |
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| Sat 9th Jan | --:-- | FL2 | Walsall | A | L | 1-2 | |
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| Sat 16th Jan | --:-- | FL2 | York City | H | W | 3-1 | |
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| Sat 23rd Jan | --:-- | AMC | Torquay United | A | W | 1-0 | |
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| Sat 30th Jan | --:-- | FL2 | Millwall | A | D | 3-3 | |
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| Sat 6th Feb | --:-- | FL2 | Chesterfield | H | W | 3-1 | |
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| Sat 13th Feb | --:-- | FL2 | Northampton Town | A | W | 1-0 | |
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| Tue 16th Feb | --:-- | AMC | Millwall | A | L | 0-1 | |
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| Sat 20th Feb | --:-- | FL2 | Colchester United | H | D | 1-1 | |
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| Tue 23rd Feb | --:-- | FL2 | Bristol Rovers | A | W | 1-0 | |
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| Sat 27th Feb | --:-- | FL2 | Burnley | A | W | 5-0 | |
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| Sat 6th Mar | --:-- | FL2 | Preston North End | H | D | 1-1 | |
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| Tue 9th Mar | --:-- | FL2 | Macclesfield Town | A | L | 0-1 | |
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| Sat 13th Mar | --:-- | FL2 | Wigan Athletic | A | L | 1-4 | |
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| Sat 20th Mar | --:-- | FL2 | Lincoln City | H | W | 4-0 | |
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| Sat 27th Mar | --:-- | FL2 | Luton Town | A | L | 0-1 | |
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| Thu 1st Apr | --:-- | FL2 | Reading | H | W | 2-1 | |
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| Mon 5th Apr | --:-- | FL2 | Wycombe Wanderers | A | W | 2-0 | |
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| Fri 9th Apr | --:-- | FL2 | AFC Bournemouth | H | W | 2-1 | |
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| Tue 13th Apr | --:-- | FL2 | Fulham | A | L | 0-3 | |
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| Sat 17th Apr | --:-- | FL2 | Manchester City | H | L | 0-2 | |
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| Tue 20th Apr | --:-- | FL2 | Wrexham | A | L | 1-2 | |
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| Sat 24th Apr | --:-- | FL2 | Oldham Athletic | A | W | 4-1 | |
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| Sat 1st May | --:-- | FL2 | Stoke City | H | W | 4-0 | |
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| Sat 8th May | --:-- | FL2 | Notts County | A | W | 1-0 | |
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| Sun 16th May | 15:00 | FL2 P/O | Preston North End | A | D | 1-1 | 18584 | |
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| Wed 19th May | 19:45 | FL2 P/O | Preston North End | H | W | 1-0 | 10105 | |
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| Sun 30th May | 15:00 | FL2 P/O | Manchester City | - | D | 2-2 | 76935 | |