| Pr. League | 01/02/97 | Wimbledon FC | - | Middlesbrough FC | 1:1 |  |
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| Pr. League | 24/10/98 | Wimbledon FC | - | Middlesbrough FC | 2:2 | ||||
| Pr. League | 05/04/99 | Middlesbrough FC | - | Wimbledon FC | 3:1 |  |
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| Pr. League | 10/08/99 | Wimbledon FC | - | Middlesbrough FC | 2:3 | ||||
| Pr. League | 27/11/99 | Middlesbrough FC | - | Wimbledon FC | 0:0 | ||||
| League Cup | 30/10/00 | Wimbledon FC | - | Middlesbrough FC | 1:0 | ||||
| FA Cup | 05/02/01 | Middlesbrough FC | - | Wimbledon FC | 0:0 | ||||
| FA Cup | 12/02/01 | Wimbledon FC | - | Middlesbrough FC | 3:1 aet | |
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| FA Cup | 07/01/02 | Wimbledon FC | - | Middlesbrough FC | 0:0 | ||||
| FA Cup | 14/01/02 | Middlesbrough FC | - | Wimbledon FC | 2:0 | ||||
| Championship | 17/09/02 | Portsmouth FC | - | Wimbledon FC | 4:1 | ||||
| League Cup | 30/09/02 | Portsmouth FC | - | Wimbledon FC | 1:3 | ||||
| Championship | 04/03/03 | Wimbledon FC | - | Portsmouth FC | 2:1 |
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