| Date & Time | Game | Venue |
|---|---|---|
| Dec. 14, 2:00 PM | (10) Martha's Vineyard Vineyarders at (0) Nantucket Whalers | Nantucket Ice Skating Rink |
| Dec. 18, 5:15 PM | (9) Mashpee/Monomoy Monarchs at (3) Nantucket Whalers | Nantucket Ice Skating Rink |
| Dec. 26, 2:00 PM | (9) North Quincy Red Raiders at (3) Nantucket Whalers
Quincy Youth Arena Holiday Tournament |
Quincy Youth Arena |
| Dec. 28, 2:00 PM | (3) Nantucket Whalers at (8) Milton Wildcats
North Quincy-Holiday Tournament |
Quincy Youth Arena |
| Jan. 8 Postponed | Dennis-Yarmouth, CC Tech, CC Academy Dolphins at Nantucket Whalers
Makeup TBD |
Nantucket Ice Skating Rink |
| Jan. 11, 1:00 PM | (0) Nantucket Whalers at (7) Northeast Tech Golden Knights | Allied Veterans Rink |
| Jan. 15, 4:00 PM | (4) Nantucket Whalers at (7) St. John Paul II Lions | Hyannis Youth and Community Center |
| Jan. 18, 1:00 PM | (1) Nantucket Whalers at (12) Somerset Berkley Raiders | Driscoll Arena |
| Jan. 25, 2:00 PM | Bourne Canalmen at Nantucket Whalers | Nantucket Ice Skating Rink |
| Jan. 29, 4:00 PM | Nantucket Whalers at Dennis-Yarmouth, CC Tech, CC Academy Dolphins | Tony Kent Arena |
| Feb. 1, 1:00 PM | Nantucket Whalers at Martha's Vineyard Vineyarders | Martha's Vineyard Arena |
| Feb. 5, 5:15 PM | St. John Paul II Lions at Nantucket Whalers | Kennedy Memorial Skating Rink |
| Feb. 8, 3:00 PM | Nantucket Whalers at Barnstable Red Hawks | Kennedy Memorial Skating Rink |
| Feb. 10, 3:00 PM | Nantucket Whalers at Bourne Canalmen | Gallo Arena |
| Feb. 12, 4:00 PM | Nantucket Whalers at Mashpee/Monomoy Monarchs | Tony Kent Arena |
| Feb. 15, 5:15 PM | Foxboro Warriors at Nantucket Whalers | Nantucket Ice Skating Rink |
| Feb. 17, 1:00 PM | Nantucket Whalers at Winthrop Vikings | Larsen Rink |
| Feb. 20 (Time TBA) | Bourne Canalmen at Nantucket Whalers | Nantucket Ice Skating Rink |
