| Date & Time | Game | Venue |
|---|---|---|
| December 10, 2023 | (3) Norwell Clippers at (2) Nantucket Whalers | Nantucket Ice Skating Rink |
| December 13, 2023 | (4) Nauset Warriors at (6) Nantucket Whalers | Nantucket Ice Skating Rink |
| December 16, 2023 | (4) Nantucket Whalers at (1) Martha's Vineyard Vineyarders | Martha's Vineyard Arena |
| December 20, 2023 | (5) Nantucket Whalers at (4) Barnstable Red Hawks | Kennedy Memorial Skating Rink |
| December 30, 2023 | (1) Framingham Flyers at (3) Nantucket Whalers | Nantucket Ice Skating Rink |
| January 03, 2024 | (4) Nantucket Whalers at (0) Dennis-Yarmouth, CC Tech, CC Academy Dolphins | Tony Kent Arena |
| January 08, 2024 | (1) St. John Paul II Lions at (7) Nantucket Whalers | Nantucket Ice Skating Rink |
| January 15, 2024 | (6) Nantucket Whalers at (1) St. John Paul II Lions | Hyannis Youth and Community Center |
| January 17, 2024 | (6) Nantucket Whalers at (4) Mashpee/Monomoy Monarchs | Tony Kent Arena |
| January 20, 2024 | (0) Bishop Stang Spartans at (5) Nantucket Whalers | Nantucket Ice Skating Rink |
| January 24, 2024 | (0) Dennis-Yarmouth, CC Tech, CC Academy Dolphins at (6) Nantucket Whalers | Nantucket Ice Skating Rink |
| January 27, 2024 | (2) Old Rochester/Fairhaven Bulldogs at (8) Nantucket Whalers | Nantucket Ice Skating Rink |
| January 31, 2024 | (4) Nantucket Whalers at (1) Old Rochester/Fairhaven Bulldogs | Falmouth Ice Arena |
| February 03, 2024 | (3) Martha's Vineyard Vineyarders at (5) Nantucket Whalers | Nantucket Ice Skating Rink |
| February 10, 2024 | (2) Nantucket Whalers at (1) Bishop Stang Spartans | Hetland Arena |
| February 11, 2024 | (0) Mashpee/Monomoy Monarchs at (5) Nantucket Whalers | Nantucket Ice Skating Rink |
| February 15, 2024 | (2) Nantucket Whalers at (6) Nauset Warriors
postponed from 2/14 |
Charles Moore Arena |
| February 19, 2024 | (1) North Reading Hornets at (1) Nantucket Whalers
Jeffrey Hayes Memorial Tournament (N. Reading wins in SO) |
Gallo Arena |
| February 20, 2024 | (0) Nantucket Whalers at (2) Sandwich Blue Knights
Jeffrey Hayes Memorial Tournament - Consolation Game |
Gallo Arena |
| February 22, 2024 | (1) Nantucket Whalers at (5) Sandwich Blue Knights | Gallo Arena |
| March 01, 2024 | (3) St. John Paul II Lions at (6) Nantucket Whalers
MIAA D4 BOYS STATE TOURNAMENT - Round 32 |
Nantucket Ice Skating Rink |
| March 03, 2024 | (2) Bourne Canalmen at (3) Nantucket Whalers
MIAA D4 BOYS STATE TOURNAMENT - Sweet 16 |
Nantucket Ice Skating Rink |
| March 06, 2024 | (4) Stoneham Spartans at (1) Nantucket Whalers
MIAA D4 BOYS STATE TOURNAMENT - Elite 8 |
Gallo Arena |
