| 2. Round | 20/09/1999 | Middlesbrough FC | - | Chesterfield FC | 2:1 |  |
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| 3. Round | 12/10/1999 | Middlesbrough FC | - | Watford FC | 1:0 | ||||
| Round of 16 | 29/11/1999 | Middlesbrough FC | - | Arsenal FC | 3:1 pso | ||||
| Quarter-finals | 13/12/1999 | Tranmere Rovers | - | Middlesbrough FC | 2:1 |
| 2. Round | 20/09/1999 | Middlesbrough FC | - | Chesterfield FC | 2:1 | |
|||
| 3. Round | 12/10/1999 | Middlesbrough FC | - | Watford FC | 1:0 | ||||
| Round of 16 | 29/11/1999 | Middlesbrough FC | - | Arsenal FC | 3:1 pso | ||||
| Quarter-finals | 13/12/1999 | Tranmere Rovers | - | Middlesbrough FC | 2:1 |
| Born: | 13.10.1967 |
| Place of birth: |
Bishop Auckland, 
England |
| Nationality: |
England
|
| Height: | 185 cm |
| Weight: | 76 kg |