3. Round | 01/01/1999 | Oldham Athletic | - | Chelsea FC | 0:2 | ||||
4. Round | 24/01/1999 | Oxford United | - | Chelsea FC | 1:1 | ||||
4. Round | 02/02/1999 | Chelsea FC | - | Oxford United | 4:2 | ||||
Round of 16 | 12/02/1999 | Sheffield Wednesday | - | Chelsea FC | 0:1 | ||||
Quarter-finals | 06/03/1999 | Manchester United | - | Chelsea FC | 0:0 | ||||
Quarter-finals | 09/03/1999 | Chelsea FC | - | Manchester United | 0:2 |