Highcliffe B
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| Home Team | Result | Away Team | Date | Time | Status |
|---|---|---|---|---|---|
| Highcliffe B | 2 - 2 | Wimborne D | Mon 17th Sep 2018 | 19:30 | OV |
| Ringwood B | 2 - 2 | Highcliffe B | Mon 1st Oct 2018 | 19:30 | OV |
| Highcliffe B | 2½ - 1½ | Poole D | Mon 22nd Oct 2018 | 19:30 | OU |
| Highcliffe B | 2½ - 1½ | Bournemouth B | Mon 19th Nov 2018 | 19:30 | OV |
| Southbourne C | 2 - 2 | Highcliffe B | Fri 14th Dec 2018 | 19:30 | OU |
| Highcliffe B | 1½ - 2½ | Southbourne C | Mon 28th Jan 2019 | 19:30 | OU |
| Bournemouth B | 1½ - 2½ | Highcliffe B | Tue 19th Feb 2019 | 19:30 | OV |
| Poole D | 2 - 2 | Highcliffe B | Thu 21st Mar 2019 | 19:30 | OV |
| Highcliffe B | 1½ - 2½ | Ringwood B | Mon 13th May 2019 | 19:30 | OV |
| Wimborne D | 2 - 2 | Highcliffe B | Wed 22nd May 2019 | 19:30 | OV |