| Pr. League | 24/03/89 | Wimbledon FC | - | Middlesbrough FC | 1:1 | ||||
| League Cup | 25/10/89 | Middlesbrough FC | - | Wimbledon FC | 1:1 | ||||
| League Cup | 07/11/89 | Wimbledon FC | - | Middlesbrough FC | 1:0 | ||||
| Pr. League | 10/12/92 | Middlesbrough FC | - | Chelsea FC | 0:0 | ||||
| Pr. League | 26/08/95 | Middlesbrough FC | - | Chelsea FC | 2:0 |  |
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| Pr. League | 21/08/96 | Chelsea FC | - | Middlesbrough FC | 1:0 | |
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| Pr. League | 22/03/97 | Middlesbrough FC | - | Chelsea FC | 1:0 | ||||
| FA Cup | 17/05/97 | Chelsea FC | - | Middlesbrough FC | 2:0 | ||||
| League Cup | 28/03/98 | Chelsea FC | - | Middlesbrough FC | 2:0 aet | |
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| Pr. League | 14/04/99 | Middlesbrough FC | - | Chelsea FC | 0:0 | ||||
| Pr. League | 25/09/99 | Middlesbrough FC | - | Chelsea FC | 0:1 | ||||
| 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 | 17/09/01 | Leicester City | - | Middlesbrough FC | 1:2 |
England