Year 11 Tameside Cup
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| Tuesday, 30 November 1999 12:00
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| Year 10 Tameside Cup | Westhill - Year 10 | 2 | - | 1 | St Damians - Year 10 | |
| Tuesday, 30 November 1999 12:00
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| Year 10 Tameside Cup | St Phillip Howard - Year 10 | 2 | - | 4 | Westhill - Year 10 | |
| Tuesday, 30 November 1999 12:00
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| Year 11 Tameside Cup | Copley - Year 11 | 0 | - | 8 | Westhill - Year 11 | |
| Tuesday, 30 November 1999 12:00
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| Year 9 Tameside Cup | Alder - Year 9 | 0 | - | 3 | Westhill - Year 9 | |
| Tuesday, 30 November 1999 12:00
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| Year 11 Tameside Cup | Audenshaw - Year 11 | 2 | - | 3 | Westhill - Year 11 | |
| Tuesday, 30 November 1999 12:00
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| Year 9 Tameside Cup | Audenshaw - Year 9 | | - | | Westhill - Year 9 | |
| Tuesday, 30 November 1999 12:00
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| Year 8 Tameside Cup | Two Trees - Year 8 | 0 | - | 4 | Westhill - Year 8 | |
| Tuesday, 30 November 1999 12:00
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| Year 11 Tameside Cup | Alder - Year 11 | 1 | - | 2 | Westhill - Year 11 | |
| Tuesday, 30 November 1999 12:00
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| Year 8 Tameside Cup | Littlemoss - Year 8 | 1 | - | 5 | Westhill - Year 8 | |
| Tuesday, 30 November 1999 12:00
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| Year 7 Tameside Cup | Westhill - Year 7 | 1 | - | 6 | Glossopdale - Year 7 | |
| Tuesday, 30 November 1999 12:00
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| Year 8 Tameside Cup | Longdendale - Year 8 | | - | | Westhill - Year 8 | |
| Tuesday, 30 November 1999 12:00
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| Year 11 Tameside Cup | Westhill - Year 11 | | - | | St Thomas More - Year 11 | |
| Tuesday, 30 November 1999 12:00
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| Year 9 Tameside Cup | Westhill - Year 9 | 3 | - | 0 | St Thomas More - Year 9 | |
| Tuesday, 30 November 1999 12:00
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| Year 8 Tameside Cup | Westhill - Year 8 | 2 | - | 0 | St Thomas More - Year 8 | |
| Tuesday, 30 November 1999 12:00
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| Year 10 Tameside Cup | Audenshaw - Year 10 | 3 | - | 0 | Westhill - Year 10 | |
| Tuesday, 30 November 1999 12:00
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| Year 9 Tameside Cup | Westhill - Year 9 | 8 | - | 0 | Two Trees - Year 9 | |
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