Associate Members' Cup
1998-1999
| Sunday 18th April 1999 | ||||||
| Final | Millwall  |
0-1 |  Wigan Athletic |
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| Tuesday 23rd March 1999 | ||||||
| Area Final Second Leg | Wrexham  |
2-3 | Wigan Athletic |
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| Tuesday 16th March 1999 | ||||||
| Area Final Second Leg | Walsall  |
1-1 | Millwall |
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| Area Final First Leg | Wigan Athletic |
2-0 | Wrexham |
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| Tuesday 9th March 1999 | ||||||
| Area Final First Leg | Millwall |
1-0 | Walsall |
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| Monday 8th March 1999 | ||||||
| Area Semi-Final | Rochdale  |
0-2 | Wigan Athletic |
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| Tuesday 23rd February 1999 | ||||||
| Area Quarter-Final | Rochdale |
2-1 |  Halifax Town |
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| Tuesday 16th February 1999 | ||||||
| Area Semi-Final | Lincoln City  |
1-2 | Wrexham |
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| Area Semi-Final | Millwall |
1-0 |  Gillingham |
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| Area Semi-Final | Walsall |
1-1 |  Cambridge United (4-3 pens) |
5087 |  |
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| Tuesday 2nd February 1999 | ||||||
| Area Quarter-Final | AFC Bournemouth  |
1-1 | Millwall |
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| Second Round | Rochdale |
2-1 |  Stoke City |
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| Tuesday 26th January 1999 | ||||||
| Area Quarter-Final | Carlisle United  |
0-3 | Wigan Athletic |
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| Area Quarter-Final | Hartlepool United  |
0-3 | Lincoln City |
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| Saturday 23rd January 1999 | ||||||
| Area Quarter-Final | Torquay United  |
0-1 | Gillingham |
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| Tuesday 19th January 1999 | ||||||
| Area Quarter-Final | Brentford  |
0-0 | Walsall |
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| Area Quarter-Final | Cambridge United |
1-1 |  Exeter City (5-3 pens) |
2741 | |
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| Second Round | Hartlepool United |
2-2 |  Preston North End |
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| Second Round | Scunthorpe United  |
1-1 | Carlisle United |
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| Second Round | Wigan Athletic |
3-0 |  Scarborough |
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| Area Quarter-Final | Wrexham |
3-2 |  Chesterfield |
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| Tuesday 12th January 1999 | ||||||
| Second Round | Darlington  |
0-2 | Chesterfield |
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| Tuesday 5th January 1999 | ||||||
| Second Round | AFC Bournemouth |
5-1 |  Peterborough United |
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| Second Round | Brighton and Hove Albion  |
1-5 | Millwall |
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| Second Round | Cambridge United |
3-2 |  Northampton Town |
2391 | |
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| Second Round | Exeter City |
3-1 |  Southend United |
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| Second Round | Halifax Town |
4-2 |  York City |
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| Second Round | Hull City  |
1-2 | Wrexham |
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| Second Round | Lincoln City |
1-0 |  Mansfield Town |
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| Second Round | Luton Town  |
0-3 | Walsall |
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| Second Round | Swansea City  |
0-1 | Gillingham |
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| Second Round | Torquay United |
2-1 |  Fulham |
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| Second Round | Wycombe Wanderers  |
1-4 | Brentford |
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| Tuesday 22nd December 1998 | ||||||
| First Round | Notts County  |
0-1 | Hull City |
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| Wednesday 9th December 1998 | ||||||
| First Round | Millwall |
2-0 |  Cardiff City |
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| Tuesday 8th December 1998 | ||||||
| First Round | AFC Bournemouth |
2-0 |  Reading |
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| First Round | Blackpool  |
0-2 | Stoke City |
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| First Round | Brentford |
2-0 |  Plymouth Argyle |
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| First Round | Burnley  |
0-1 | Preston North End |
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| First Round | Chester City  |
1-2 | Hartlepool United |
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| First Round | Macclesfield Town  |
0-1 | Wrexham |
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| First Round | Manchester City  |
1-2 | Mansfield Town |
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| First Round | Oldham Athletic  |
0-1 | Darlington |
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| First Round | Peterborough United |
3-0 |  Leyton Orient |
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| First Round | Rotherham United  |
0-3 | Wigan Athletic |
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| First Round | Shrewsbury Town  |
0-1 | Wycombe Wanderers |
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| First Round | Swansea City |
4-1 |  Barnet |
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| First Round | Walsall |
2-2 |  Bristol Rovers |
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| Saturday 5th December 1998 | ||||||
| First Round | Colchester United  |
1-5 | Gillingham |
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