| 26. Round | 20/02/1999 | Southampton FC | - | Newcastle United | 2:1 | ||||
| 27. Round | 27/02/1999 | Manchester United | - | Southampton FC | 2:1 | ||||
| 25. Round | 02/03/1999 | Tottenham Hotspur | - | Southampton FC | 3:0 | ||||
| 31. Round | 03/04/1999 | Southampton FC | - | Arsenal FC | 0:0 | ||||
| 32. Round | 05/04/1999 | Coventry City | - | Southampton FC | 1:0 | ||||
| 33. Round | 10/04/1999 | Aston Villa | - | Southampton FC | 3:0 | ||||
| 34. Round | 17/04/1999 | Southampton FC | - | Blackburn Rovers | 3:3 |  |
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| 36. Round | 01/05/1999 | Southampton FC | - | Leicester City | 2:1 | ||||
| 37. Round | 08/05/1999 | Wimbledon FC | - | Southampton FC | 0:2 |
Wales