First Round
15/01/2019 |
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2nd Round
12/02/2019 |
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Quarter Final
02/04/2019 |
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NW Semi Final
09/04/2019 |
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| Blackheath 4 | 0 | | (5-0) Full Result | | Old Wilsonians 1 (h) | 5 | | Match 1 |
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| Old Wilsonians 1 | 5 | | (5-0) Full Result | | Parklangley 4 | 0 | | Match 9 |
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| Old Wilsonians 1 | | | | | Bromley Sports 2 | | | Match 13 |
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| Nuffield Health 1 | 5 | | (0-5) Full Result | | Nuffield Health 2 (h) | 0 | | Match 3 |
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| Nuffield Health 1 | 1 | | (1-4) Full Result | | Bromley Sports 2 | 4 | | Match 10 |
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| Bromley Sports 2 | 5 | | (0-5) Full Result | | Bromley Sports 3 (h) | 0 | | Match 4 |
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| Bexley 5 | | | | | Tunbridge Wells SRC 3 (h) | | | Match 5 |
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| Waterfront 1 | | | | | Sydenham 1 (h) | | | Match 6 |
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| Tunbridge Wells SRC 4 | 1 | | (4-1) Full Result | | Sundridge Park 2 (h) | 4 | | Match 7 |
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| Bexley 4 | 5 | | (0-5) Full Result | | Wells Squash Club 1 (h) | 0 | | Match 8 |
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