| Date & Time | Game | Venue |
|---|---|---|
| January 02, 2021 | (3) Nantucket Whalers at (0) Nauset Warriors | Charles Moore Arena |
| Jan. 9 Postponed | Mashpee/Monomoy Monarchs at Nantucket Whalers
make up tbd |
Nantucket Ice Skating Rink |
| January 10, 2021 | (1) Nantucket Whalers at (0) Norwell Clippers | Hetland Arena |
| January 16, 2021 | (0) Dennis-Yarmouth, CC Tech, CC Academy Dolphins at (3) Nantucket Whalers | Nantucket Ice Skating Rink |
| January 18, 2021 | (3) Sandwich Blue Knights at (3) Nantucket Whalers | Nantucket Ice Skating Rink |
| January 20, 2021 | (4) Nantucket Whalers at (1) St. John Paul II Lions | Kennedy Memorial Skating Rink |
| Jan. 23 Postponed | Bishop Stang Spartans at Nantucket Whalers | Nantucket Ice Skating Rink |
| January 30, 2021 | (5) Nantucket Whalers at (4) Falmouth Clippers | Falmouth Ice Arena |
| February 03, 2021 | (6) Nantucket Whalers at (0) Mashpee/Monomoy Monarchs | Tony Kent Arena |
| February 06, 2021 | (5) Nantucket Whalers at (1) Martha's Vineyard Vineyarders | Martha's Vineyard Arena |
| February 08, 2021 | (5) Bishop Stang Spartans at (1) Nantucket Whalers | Nantucket Ice Skating Rink |
| February 13, 2021 | (4) Nantucket Whalers at (0) Dennis-Yarmouth, CC Tech, CC Academy Dolphins
TIME UPDATED |
Tony Kent Arena |
| February 15, 2021 | (3) Nantucket Whalers at (5) Sandwich Blue Knights | Gallo Arena |
| February 17, 2021 | (3) St. John Paul II Lions at (5) Nantucket Whalers | Nantucket Ice Skating Rink |
| February 20, 2021 | (7) Martha's Vineyard Vineyarders at (1) Nantucket Whalers | Nantucket Ice Skating Rink |
| February 25, 2021 | (1) St. John Paul II Lions at (3) Nantucket Whalers
Boys Cape Cod Cup Playoff Game |
Nantucket Ice Skating Rink |
| February 27, 2021 | (1) Dennis-Yarmouth, CC Tech, CC Academy Dolphins at (3) Nantucket Whalers
Boys Cape Cod Cup Lighthouse Championship |
Nantucket Ice Skating Rink |
