Highcliffe C
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| Home Team | Result | Away Team | Date | Time | Status |
|---|---|---|---|---|---|
| Ringwood B | 3 - 1 | Highcliffe C | Mon 30th Sep 2019 | 19:30 | OU |
| Highcliffe C | 1 - 3 | Southbourne C | Mon 14th Oct 2019 | 19:30 | OV |
| Poole C | 4 - 0 | Highcliffe C | Thu 24th Oct 2019 | 19:30 | OV |
| Highcliffe C | 2½ - 1½ | Wimborne D | Mon 4th Nov 2019 | 19:30 | OU |
| New Milton B | 3 - 1 | Highcliffe C | Tue 19th Nov 2019 | 19:30 | OV |
| Highcliffe C | 3 - 1 | New Milton B | Mon 20th Jan 2020 | 19:30 | OV |
| Wimborne D | 3 - 1 | Highcliffe C | Wed 19th Feb 2020 | 19:30 | OU |
| Highcliffe C | 0 - 0 | Poole C | Postponed | 19:30 | OU |
| Southbourne C | 0 - 0 | Highcliffe C | Fri 17th Apr 2020 | 19:30 | OU |
| Highcliffe C | 0 - 0 | Ringwood B | Mon 11th May 2020 | 19:30 | OU |