Ipswich Town
1998-1999
[squad stats] [appearance chart]
| Date | K.O. | Comp | Opponents | Ven | Res | Att | ||||
| Sun 9th Aug | --:-- | FL1 | Grimsby Town | A | D | 0-0 |  |
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| Tue 11th Aug | --:-- | LC | Exeter City | A | D | 1-1 | |
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| Sat 15th Aug | --:-- | FL1 | Bury | H | D | 0-0 | |
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| Tue 18th Aug | --:-- | LC | Exeter City | H | W | 5-1 | |
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| Sat 22nd Aug | --:-- | FL1 | Portsmouth | A | D | 0-0 | |
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| Sat 29th Aug | --:-- | FL1 | Sunderland | H | L | 0-2 | |
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| Mon 31st Aug | --:-- | FL1 | Port Vale | A | W | 3-0 | |
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| Tue 8th Sep | --:-- | FL1 | Bradford City | H | W | 3-0 | |
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| Sat 12th Sep | --:-- | FL1 | Oxford United | A | D | 3-3 | |
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| Tue 15th Sep | --:-- | LC | Luton Town | H | W | 2-1 | |
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| Sat 19th Sep | --:-- | FL1 | Bristol City | H | W | 3-1 | |
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| Tue 22nd Sep | --:-- | LC | Luton Town | A | L | 2-4 | |
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| Sat 26th Sep | --:-- | FL1 | Watford | A | L | 0-1 | |
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| Tue 29th Sep | --:-- | FL1 | Tranmere Rovers | A | W | 2-0 | |
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| Sat 3rd Oct | --:-- | FL1 | Crystal Palace | H | W | 3-0 | |
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| Sat 17th Oct | --:-- | FL1 | Swindon Town | H | W | 1-0 | |
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| Tue 20th Oct | --:-- | FL1 | Norwich City | H | L | 0-1 | |
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| Sat 24th Oct | --:-- | FL1 | Stockport County | A | W | 1-0 | |
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| Sat 31st Oct | --:-- | FL1 | West Bromwich Albion | H | W | 2-0 | |
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| Tue 3rd Nov | --:-- | FL1 | Wolverhampton Wanderers | H | W | 2-0 | |
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| Sat 7th Nov | --:-- | FL1 | Huddersfield Town | A | D | 2-2 | |
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| Sat 14th Nov | --:-- | FL1 | Barnsley | A | W | 1-0 | |
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| Sat 21st Nov | --:-- | FL1 | Bolton Wanderers | H | L | 0-1 | |
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| Sat 28th Nov | --:-- | FL1 | Crewe Alexandra | A | W | 3-0 | |
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| Wed 2nd Dec | --:-- | FL1 | Queens Park Rangers | A | D | 1-1 | |
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| Sat 5th Dec | --:-- | FL1 | Birmingham City | H | W | 1-0 | |
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| Sat 12th Dec | --:-- | FL1 | Barnsley | H | L | 0-2 | |
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| Sun 20th Dec | --:-- | FL1 | Sheffield United | A | W | 2-1 | |
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| Sat 26th Dec | --:-- | FL1 | Portsmouth | H | W | 3-0 | |
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| Mon 28th Dec | --:-- | FL1 | Wolverhampton Wanderers | A | L | 0-1 | |
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| Sat 2nd Jan | --:-- | FAC | Tranmere Rovers | A | W | 1-0 | |
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| Sat 9th Jan | --:-- | FL1 | Grimsby Town | H | L | 0-1 | |
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| Sun 17th Jan | --:-- | FL1 | Sunderland | A | L | 1-2 | |
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| Sat 23rd Jan | --:-- | FAC | Everton | A | L | 0-1 | |
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| Sat 30th Jan | --:-- | FL1 | Port Vale | H | W | 1-0 | |
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| Sat 6th Feb | --:-- | FL1 | Bury | A | W | 3-0 | |
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| Sat 13th Feb | --:-- | FL1 | Bradford City | A | D | 0-0 | |
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| Sat 20th Feb | --:-- | FL1 | Oxford United | H | W | 2-1 | |
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| Sat 27th Feb | --:-- | FL1 | Bristol City | A | W | 1-0 | |
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| Tue 2nd Mar | --:-- | FL1 | Watford | H | W | 3-2 | |
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| Sat 6th Mar | --:-- | FL1 | Tranmere Rovers | H | W | 1-0 | |
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| Tue 9th Mar | --:-- | FL1 | Crystal Palace | A | L | 2-3 | |
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| Sat 13th Mar | --:-- | FL1 | Huddersfield Town | H | W | 3-0 | |
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| Sat 20th Mar | --:-- | FL1 | West Bromwich Albion | A | W | 1-0 | |
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| Sat 3rd Apr | --:-- | FL1 | Swindon Town | A | W | 6-0 | |
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| Mon 5th Apr | --:-- | FL1 | Queens Park Rangers | H | W | 3-1 | |
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| Sun 11th Apr | --:-- | FL1 | Norwich City | A | D | 0-0 | |
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| Sat 17th Apr | --:-- | FL1 | Bolton Wanderers | A | L | 0-2 | |
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| Tue 20th Apr | --:-- | FL1 | Stockport County | H | W | 1-0 | |
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| Sat 24th Apr | --:-- | FL1 | Crewe Alexandra | H | L | 1-2 | |
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| Sun 2nd May | --:-- | FL1 | Birmingham City | A | L | 0-1 | |
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| Sun 9th May | --:-- | FL1 | Sheffield United | H | W | 4-1 | |
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| Sun 16th May | 13:00 | FL1 P/O | Bolton Wanderers | A | L | 0-1 | 18295 | |
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| Wed 19th May | 19:45 | FL1 P/O | Bolton Wanderers | H | W | 4-3 | 21755 | |