| Pr. League | 31.03.01 | Chelsea | - | Middlesbrough | 2:1 | ||||
| Pr. League | 27.04.02 | Middlesbrough | - | Chelsea | 0:2 | ||||
| Pr. League | 16.11.02 | Chelsea | - | Middlesbrough | 1:0 | ||||
| Pr. League | 14.12.02 | Middlesbrough | - | Chelsea | 1:1 | ||||
| FA Cup | 04.01.03 | Chelsea | - | Middlesbrough | 1:0 |  |
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| Pr. League | 05.10.03 | Middlesbrough | - | Chelsea | 1:2 | ||||
| Pr. League | 23.08.06 | Middlesbrough | - | Chelsea | 2:1 | ||||
| Pr. League | 30.03.08 | Chelsea | - | Middlesbrough | 1:0 | ||||
| Pr. League | 18.10.08 | Middlesbrough | - | Chelsea | 0:5 |
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