| Saturday 11th November, 1989 |
| East Riding Senior Cup First Round |
| Bridlington Trinity |  | 1-2 |  | Bridlington Town | |
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| Saturday 9th December, 1989 |
| East Riding Senior Cup Second Round |
| Hall Road Rangers |  | 1-2 |  | North Ferriby United | |
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| Tuesday 12th December, 1989 |
| East Riding Senior Cup Second Round |
| Bridlington Town | | 4-0 |  | Hull OG | |
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| Tuesday 13th February, 1990 |
| East Riding Senior Cup Third Round |
| Bridlington Town | | 4-0 | | Ideal Standard | |
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| Thursday 8th March, 1990 |
| East Riding Senior Cup Third Round |
| North Ferriby United | | 1-2 | | Hull City Res | |
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| Tuesday 10th April, 1990 |
| East Riding Senior Cup Semi-Finals |
| Bridlington Town | | 2-0 | | Hull Teachers | |
| (at N Fds) |
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| Monday 7th May, 1990 |
| East Riding Senior Cup Final |
| Bridlington Town | | 1-7 | | Hull City Res | |
| (at Hull City FC) |