New Milton C
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| Home Team | Result | Away Team | Date | Time | Status |
|---|---|---|---|---|---|
| New Milton C | 2½ - 1½ | Poole E | Tue 15th Oct 2019 | 19:30 | OU |
| Highcliffe E | 2 - 2 | New Milton C | Mon 28th Oct 2019 | 19:30 | OU |
| Bournemouth C | ½ - 3½ | New Milton C | Tue 5th Nov 2019 | 19:30 | OV |
| New Milton C | 3 - 1 | Southbourne E | Tue 26th Nov 2019 | 19:30 | OU |
| Southbourne E | 1½ - 2½ | New Milton C | Fri 10th Jan 2020 | 19:30 | OV |
| Wimborne F | 2½ - 1½ | New Milton C | Wed 15th Jan 2020 | 19:30 | OU |
| New Milton C | 1½ - 2½ | Bournemouth C | Tue 18th Feb 2020 | 19:30 | OV |
| New Milton C | 4 - 0 | Highcliffe E | Tue 17th Mar 2020 | 19:30 | OU |
| Poole E | 0 - 0 | New Milton C | Thu 9th Apr 2020 | 19:30 | OU |
| New Milton C | 0 - 0 | Wimborne F | Tue 19th May 2020 | 19:30 | OU |