| Date & Time | Game | Venue |
|---|---|---|
| December 18, 2019 | (1) Old Rochester/Fairhaven Bulldogs at (4) Nantucket Whalers | Nantucket Ice Skating Rink |
| December 21, 2019 | (4) Norwood Mustangs at (3) Nantucket Whalers | Nantucket Ice Skating Rink |
| December 30, 2019 | (2) Nantucket Whalers at (3) Ashland Clockers | Gallo Arena |
| January 02, 2020 | (3) Bishop Stang Spartans at (4) Nantucket Whalers
game postponed due to poor weather/travel conditions |
Nantucket Ice Skating Rink |
| January 04, 2020 | (1) Nantucket Whalers at (4) Holliston Panthers | Loring Arena |
| January 09, 2020 | (2) Mashpee/Monomoy Monarchs at (4) Nantucket Whalers | Nantucket Ice Skating Rink |
| January 11, 2020 | (2) Nantucket Whalers at (0) Martha's Vineyard Vineyarders
Rivalry Game |
Martha's Vineyard Arena |
| January 14, 2020 | (1) Sandwich Blue Knights at (2) Nantucket Whalers
rescheduled and played on 1/14 |
Nantucket Ice Skating Rink |
| January 18, 2020 | (0) Nantucket Whalers at (2) Bishop Stang Spartans | Hetland Arena |
| January 20, 2020 | (4) Nantucket Whalers at (1) Old Rochester/Fairhaven Bulldogs | Travis Roy Arena |
| January 22, 2020 | (2) Nantucket Whalers at (0) Dennis-Yarmouth, CC Tech, CC Academy Dolphins | Tony Kent Arena |
| January 29, 2020 | (7) Nantucket Whalers at (1) Mashpee/Monomoy Monarchs | Hyannis Youth and Community Center |
| January 30, 2020 | (6) Nantucket Whalers at (1) Cardinal Spellman Cardinals | Zapustas Arena |
| February 01, 2020 | (6) Norwell Clippers at (2) Nantucket Whalers | Nantucket Ice Skating Rink |
| February 06, 2020 | (0) Dennis-Yarmouth, CC Tech, CC Academy Dolphins at (3) Nantucket Whalers
make up from 1-25 |
Tony Kent Arena |
| February 08, 2020 | (3) Martha's Vineyard Vineyarders at (4) Nantucket Whalers
Rivalry Game |
Nantucket Ice Skating Rink |
| February 12, 2020 | (2) Nantucket Whalers at (2) Sandwich Blue Knights | Gallo Arena |
| February 17, 2020 | (2) Nantucket Whalers at (2) Marblehead Magicians
Jeffrey Hayes Memorial Tournament |
Gallo Arena |
| February 18, 2020 | (1) Sandwich Blue Knights at (4) Nantucket Whalers
JEFF HAYES TOURNEY Consolation Game |
Gallo Arena |
| February 20, 2020 | (1) Nantucket Whalers at (4) Norwell Clippers | Gallo Arena |
| February 28, 2020 | (5) Bishop Stang Spartans at (2) Nantucket Whalers
Boys D3 S Playoff |
Gallo Arena |
