| Date & Time | Game | Venue |
|---|---|---|
| December 18, 2019 | (2) Nantucket Whalers at (11) Dennis-Yarmouth Dolphins | Tony Kent Arena |
| December 21, 2019 | (9) Barnstable Red Hawks at (1) Nantucket Whalers | Nantucket Ice Skating Rink |
| January 04, 2020 | (4) Nantucket Whalers at (8) Martha's Vineyard Vineyarders | Martha's Vineyard Arena |
| January 11, 2020 | (10) Falmouth Clippers at (2) Nantucket Whalers | Nantucket Ice Skating Rink |
| January 15, 2020 | (10) Nauset/Monomoy Warriors at (5) Nantucket Whalers | Nantucket Ice Skating Rink |
| January 22, 2020 | (1) Nantucket Whalers at (8) Sandwich Lady Knights | Gallo Arena |
| January 26, 2020 | (11) Dennis-Yarmouth Dolphins at (1) Nantucket Whalers
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Nantucket Ice Skating Rink |
| January 29, 2020 | (0) Nantucket Whalers at (4) Barnstable Red Hawks | Kennedy Memorial Skating Rink |
| February 01, 2020 | (4) Martha's Vineyard Vineyarders at (3) Nantucket Whalers | Nantucket Ice Skating Rink |
| February 05, 2020 | (1) Nantucket Whalers at (6) Falmouth Clippers | Falmouth Ice Arena |
| February 08, 2020 | (0) Nantucket Whalers at (5) Nauset/Monomoy Warriors | Charles Moore Arena |
| February 15, 2020 | (7) Sandwich Lady Knights at (0) Nantucket Whalers | Gallo Arena |
