| Pr. League | 22.04.00 | Chelsea FC | - | Middlesbrough FC | 1:1 | ||||
| Pr. League | 16.12.00 | Middlesbrough FC | - | Chelsea FC | 1:0 | ||||
| Pr. League | 31.03.01 | Chelsea FC | - | Middlesbrough FC | 2:1 | ||||
| Pr. League | 23.09.01 | Chelsea FC | - | Middlesbrough FC | 2:2 |  |
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| Pr. League | 27.04.02 | Middlesbrough FC | - | Chelsea FC | 0:2 | ||||
| Pr. League | 16.11.02 | Chelsea FC | - | Middlesbrough FC | 1:0 | |
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| Pr. League | 14.12.02 | Middlesbrough FC | - | Chelsea FC | 1:1 | ||||
| FA Cup | 04.01.03 | Chelsea FC | - | Middlesbrough FC | 1:0 | ||||
| Pr. League | 11.09.04 | Middlesbrough FC | - | Birmingham City | 2:1 | ||||
| Pr. League | 26.12.04 | Birmingham City | - | Middlesbrough FC | 2:0 | ||||
| Pr. League | 23.08.05 | Birmingham City | - | Middlesbrough FC | 0:3 | ||||
| Pr. League | 04.03.06 | Middlesbrough FC | - | Birmingham City | 1:0 | ||||
| Pr. League | 15.08.07 | Wigan Athletic | - | Middlesbrough FC | 1:0 | ||||
| Pr. League | 29.01.08 | Middlesbrough FC | - | Wigan Athletic | 1:0 | ||||
| Pr. League | 04.10.08 | Wigan Athletic | - | Middlesbrough FC | 0:1 | ||||
| Pr. League | 21.02.09 | Middlesbrough FC | - | Wigan Athletic | 0:0 |
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