| Pr. League | 24.10.98 | Wimbledon FC | - | Middlesbrough FC | 2:2 |  |
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| 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 | |
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| Pr. League | 27.11.99 | Middlesbrough FC | - | Wimbledon FC | 0:0 | ||||
| League Cup | 31.10.00 | Wimbledon FC | - | Middlesbrough FC | 1:0 | ||||
| FA Cup | 06.02.01 | Middlesbrough FC | - | Wimbledon FC | 0:0 |  |
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| FA Cup | 13.02.01 | Wimbledon FC | - | Middlesbrough FC | 3:1 n.V. | |
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| FA Cup | 08.01.02 | Wimbledon FC | - | Middlesbrough FC | 0:0 |
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