Highcliffe B
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| Home Team | Result | Away Team | Date | Time | Status |
|---|---|---|---|---|---|
| Dorchester C | 1½ - 2½ | Highcliffe B | Thu 26th Sep 2019 | 19:30 | OV |
| Weymouth B | 2 - 2 | Highcliffe B | Thu 7th Nov 2019 | 19:30 | OU |
| Highcliffe B | 2 - 2 | Dorchester B | Mon 25th Nov 2019 | 19:30 | OV |
| Wimborne B | 3 - 1 | Highcliffe B | Wed 27th Nov 2019 | 19:30 | OV |
| Highcliffe B | 2½ - 1½ | Purbeck A | Mon 2nd Dec 2019 | 19:30 | OV |
| Purbeck A | 2 - 2 | Highcliffe B | Mon 6th Jan 2020 | 19:30 | OV |
| Highcliffe B | 3 - 1 | Wimborne B | Mon 17th Feb 2020 | 19:30 | OV |
| Highcliffe B | 0 - 0 | Weymouth B | Postponed | 19:30 | OU |
| Dorchester B | 0 - 0 | Highcliffe B | Thu 2nd Apr 2020 | 19:30 | OU |
| Highcliffe B | 0 - 0 | Dorchester C | Mon 27th Apr 2020 | 19:30 | OU |