New Milton B
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| Home Team | Result | Away Team | Date | Time | Status |
|---|---|---|---|---|---|
| New Milton B | 2½ - 1½ | Highcliffe C | Tue 25th Sep 2018 | 19:30 | OV |
| New Milton B | 3 - 1 | Purbeck | Thu 11th Oct 2018 | 19:30 | OV |
| Wimborne E | 1½ - 2½ | New Milton B | Wed 24th Oct 2018 | 19:30 | OV |
| New Milton B | 2 - 2 | Southbourne D | Tue 20th Nov 2018 | 19:30 | OV |
| Poole E | 1 - 3 | New Milton B | Thu 13th Dec 2018 | 19:30 | OU |
| New Milton B | 2 - 2 | Poole E | Tue 22nd Jan 2019 | 19:30 | OV |
| Southbourne D | 1½ - 2½ | New Milton B | Fri 1st Mar 2019 | 19:30 | OV |
| New Milton B | 1½ - 2½ | Wimborne E | Tue 26th Mar 2019 | 19:30 | OV |
| Purbeck | 1 - 3 | New Milton B | Thu 2nd May 2019 | 19:30 | OV |
| Highcliffe C | 1½ - 2½ | New Milton B | Mon 13th May 2019 | 19:30 | OV |