| 1. Round | 16/08/1998 | Southampton FC | - | Liverpool FC | 1:2 | ||||
| 2. Round | 22/08/1998 | Charlton Athletic | - | Southampton FC | 5:0 | ||||
| 3. Round | 29/08/1998 | Southampton FC | - | Nottingham Forest | 1:2 | ||||
| 14. Round | 21/11/1998 | Blackburn Rovers | - | Southampton FC | 0:2 |  |
| 1. Round | 16/08/1998 | Southampton FC | - | Liverpool FC | 1:2 | ||||
| 2. Round | 22/08/1998 | Charlton Athletic | - | Southampton FC | 5:0 | ||||
| 3. Round | 29/08/1998 | Southampton FC | - | Nottingham Forest | 1:2 | ||||
| 14. Round | 21/11/1998 | Blackburn Rovers | - | Southampton FC | 0:2 | |
| Richard Andrew Dryden | |
| Born: | 14.06.1969 |
| Place of birth: |
Stroud, 
England |
| Nationality: |
England
|
| Height: | 183 cm |
| Weight: | 71 kg |