Highcliffe D
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| Home Team | Result | Away Team | Date | Time | Status |
|---|---|---|---|---|---|
| Bournemouth B | 2 - 2 | Highcliffe D | Tue 24th Sep 2019 | 19:30 | OV |
| Purbeck | 1½ - 2½ | Highcliffe D | Mon 14th Oct 2019 | 19:30 | OU |
| Highcliffe D | 3 - 1 | Southbourne D | Mon 28th Oct 2019 | 19:30 | OU |
| Highcliffe D | 2 - 2 | Poole D | Mon 25th Nov 2019 | 19:30 | OV |
| Wimborne E | 2½ - 1½ | Highcliffe D | Wed 11th Dec 2019 | 19:30 | OV |
| Highcliffe D | 2½ - 1½ | Wimborne E | Mon 27th Jan 2020 | 19:30 | OV |
| Poole D | 3 - 1 | Highcliffe D | Thu 27th Feb 2020 | 19:30 | OV |
| Highcliffe D | 0 - 0 | Purbeck | Mon 23rd Mar 2020 | 19:30 | OU |
| Southbourne D | 0 - 0 | Highcliffe D | Fri 1st May 2020 | 19:30 | OU |
| Highcliffe D | 0 - 0 | Bournemouth B | Mon 18th May 2020 | 19:30 | OU |