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GMT 01:00
| 29.05.1999 | |||
| 16:00 | Leyton Orient | 0-1 | Scunthorpe United |
| 19.05.1999 | |||
| 16:00 | Rotherham | 0-0/p.2-4 | Leyton Orient |
| 16:00 | Scunthorpe United | 3-1 AET | Swansea City |
| 16.05.1999 | |||
| 16:00 | Leyton Orient | 0-0 | Rotherham |
| 16:00 | Swansea City | 1-0 | Scunthorpe United |
| 08.05.1999 | |||
| 16:00 | Brighton | 1-1 | Rochdale |
| 16:00 | Cambridge United | 0-1 | Brentford FC |
| 16:00 | Carlisle United | 2-1 | Plymouth Argyle |
| 16:00 | Chester FC | 1-1 | Rotherham |
| 16:00 | Exeter City | 2-1 | Halifax |
| 16:00 | Leyton Orient | 2-2 | Barnet |
| 16:00 | Mansfield | 3-0 | Cardiff City |
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