1999-05-19
| Cup and International Matches |
| Division 1 Play off 2nd Leg | Venue |
Gate |
Notes |
| D 1 | Ipswich Town | 4 | 3 | Bolton Wanderers | D 1 | Portman Road | 10,505 | agg 4-4 away goal rule |
| Holland 2, Dyer 2 | Lineups | Taylor 2, Fransen | | | | |
| Division 2 Play off 2nd Leg | Venue |
Gate |
Notes |
| D 2 | Gillingham | 1 | 0 | Preston North End | D 2 | Priestfield Stadium | 21,755 | agg 2-1 |
| Hessenthaler | Lineups | | | | | |
| D 2 | Manchester City | 1 | 0 | Wigan Athletic | D 2 | Maine Road | 31,305 | agg 2-1 |
| Goater | Lineups | | | | | |
| Division 3 Play off 2nd Leg | Venue |
Gate |
Notes |
| D 3 | Rotherham United | 0 | 0 | Leyton Orient | D 3 | Millmoor | 9,529 | aet agg 0-0 4-2p |
| | Lineups | | | | | |
| D 3 | Scunthorpe United | 3 | 1 | Swansea City | D 3 | Glanford Park | 7,089 | agg 3-2 |
| Dawson, Sheldon 2 | Lineups | Bird | | | | |
