| Day | Date | From | To | Type | Location | Opponent / Sharing With |
|---|---|---|---|---|---|---|
| Tuesday | March 28, 2023 | 7:15 PM | 8:15 PM | Practice | Trinity Pawlin | |
| Wednesday | March 29, 2023 | 7:15 PM | 8:15 PM | Practice | Trinity Pawlin | |
| Thursday | March 30, 2023 | 7:15 PM | 8:15 PM | Practice | Trinity Pawlin | |
| Saturday | April 1, 2023 | 12:15 PM | 12:45 PM | Practice | Trinity Pawlin | Pee Wee |
| Saturday | April 15, 2023 | 12:15 PM | 12:45 PM | Practice | Trinity Pawlin | Pee Wee |
| Wednesday | July 19, 2023 | 7:50 PM | 8:50 PM | Practice | Brewster Ice 98 | Pee Wee |
| Wednesday | July 26, 2023 | 7:50 PM | 8:50 PM | Practice | Brewster Ice 98 | Pee Wee |
| Wednesday | August 2, 2023 | 7:50 PM | 8:50 PM | Practice | Brewster Ice 98 | Pee Wee |
| Wednesday | August 9, 2023 | 7:50 PM | 8:50 PM | Practice | Brewster Ice 98 | Pee Wee |
| Wednesday | August 16, 2023 | 7:50 PM | 8:50 PM | Practice | Brewster Ice 98 | Pee Wee |
| Wednesday | August 23, 2023 | 7:00 PM | 7:45 PM | Meeting | Brewster Ice Arena | |
| Wednesday | August 23, 2023 | 7:50 PM | 9:20 PM | Practice | Brewster Ice 98 | |
| Sunday | August 27, 2023 | 3:30 PM | 4:30 PM | Practice | Brewster Ice 98 | |
| Wednesday | August 30, 2023 | 6:40 PM | 8:10 PM | Practice | Brewster Ice 98 | |
| Wednesday | September 6, 2023 | 7:00 PM | 7:30 PM | Meeting | Brewster Ice Arena | |
| Wednesday | September 6, 2023 | 7:40 PM | 8:40 PM | Practice | Brewster Ice 98 | Pee Wee |
| Thursday | September 7, 2023 | 6:00 PM | 7:00 PM | Other | ZOOM | |
| Friday | September 8, 2023 | 7:10 PM | 8:10 PM | Practice | Brewster Ice 99 | Pee Wee |
| Sunday | September 10, 2023 | 5:00 PM | 6:30 PM | Game | Brewster Ice Arena | vs. Scarsdale A |
| Wednesday | September 13, 2023 | 7:40 PM | 8:40 PM | Practice | Brewster Ice 98 | Pee Wee |
| Saturday | September 16, 2023 | 2:40 PM | 4:10 PM | Game | Brewster Ice Arena | vs. Mamaroneck |
| Sunday | September 17, 2023 | 11:00 AM | 12:30 PM | Game | Brewster Ice Arena | vs. Rye Rangers A |
| Wednesday | September 20, 2023 | 7:40 PM | 8:40 PM | Practice | Brewster Ice 98 | Pee Wee |
| Friday | September 22, 2023 | 7:10 PM | 8:10 PM | Practice | Brewster Ice 99 | Pee Wee |
| Saturday | September 23, 2023 | 5:15 PM | 6:30 PM | Game | Danbury Liberty | @ Western 14U A1 - Open |
| Sunday | September 24, 2023 | 6:30 PM | 8:00 PM | Game | Brewster Ice 1 | vs. Darien 14U B |
| Wednesday | September 27, 2023 | 7:40 PM | 8:40 PM | Practice | Brewster Ice 98 | Pee Wee |
| Saturday | September 30, 2023 | 2:00 PM | 3:30 PM | Game | Trinity-Pawlin Rink | vs. Wallingford 14U A - Open |
| Sunday | October 1, 2023 | 4:20 PM | 5:50 PM | Game | Westchester Skating Academy | @ Scarsdale A |
| Wednesday | October 4, 2023 | 7:15 PM | 8:15 PM | Practice | Trinity Pawlin | Pee Wee |
| Saturday | October 7, 2023 | 10:30 AM | 12:00 PM | Game | Trinity-Pawlin Rink | vs. Junior Bulldogs 14U A |
| Wednesday | October 11, 2023 | 7:15 PM | 8:15 PM | Practice | Trinity Pawlin | Pee Wee |
| Saturday | October 14, 2023 | 4:30 PM | 5:50 PM | Game | Darien Ice House | @ New Canaan Winter Club 14U A1 |
| Wednesday | October 18, 2023 | 7:15 PM | 8:15 PM | Practice | Trinity Pawlin | Pee Wee |
| Thursday | October 19, 2023 | 7:00 PM | 8:00 PM | Other | Zoom | |
| Friday | October 20, 2023 | 7:10 PM | 8:10 PM | Practice | Brewster Ice 99 | Pee Wee |
| Saturday | October 21, 2023 | 6:15 PM | 7:45 PM | Game | Ice Time Sports Complex | @ Polar Bears A |
| Sunday | October 22, 2023 | 11:00 AM | 12:30 PM | Other | Brewster Ice Arena | |
| Wednesday | October 25, 2023 | 7:15 PM | 8:15 PM | Practice | Trinity Pawlin | Pee Wee |
| Friday | October 27, 2023 | 3:15 PM | 4:15 PM | Game | Twin Ponds Arena | @ North Stars |
| Friday | October 27, 2023 | 8:30 PM | 9:30 PM | Game | Twin Ponds Arena | @ Campus Wild |
| Saturday | October 28, 2023 | 12:10 PM | 1:10 PM | Game | 3904 Corey Rd | vs. Bowie Bruins |
| Sunday | October 29, 2023 | 10:20 AM | 11:50 AM | Game | Klick Lewis Arena | vs. North stars |
| Sunday | October 29, 2023 | 4:30 PM | 6:00 PM | Game | Twin Ponds Arena | vs. SHAHA |
| Wednesday | November 1, 2023 | 6:50 PM | 7:50 PM | Other | Trinity-Pawling School | |
| Wednesday | November 1, 2023 | 7:15 PM | 8:15 PM | Practice | Trinity Pawlin | Pee Wee |
| Friday | November 3, 2023 | 7:10 PM | 8:10 PM | Practice | Brewster Ice 99 | Midget |
| Saturday | November 4, 2023 | 6:30 PM | 8:00 PM | Game | Trinity-Pawlin Rink | vs. Western 14U A1 - Open |
| Wednesday | November 8, 2023 | 7:15 PM | 8:15 PM | Practice | Trinity Pawlin | Pee Wee |
| Sunday | November 12, 2023 | 5:45 PM | 7:15 PM | Game | Trinity-Pawlin Rink | vs. Ridgefield 14U A1 |
| Wednesday | November 15, 2023 | 7:15 PM | 8:15 PM | Practice | Trinity Pawlin | Pee Wee |
| Thursday | November 16, 2023 | 6:00 PM | 7:00 PM | Meeting | Zoom | |
| Saturday | November 18, 2023 | 4:00 PM | 5:30 PM | Game | Trinity-Pawling School | @ Polar Bears A |
| Sunday | November 19, 2023 | 10:50 AM | 12:20 PM | Game | Terry Conners Rink | @ Stamford 14U A1 |
| Friday | November 24, 2023 | 7:20 PM | 8:40 PM | Practice | Brewster Ice 98 | Pee Wee |
| Saturday | November 25, 2023 | 1:00 PM | 2:30 PM | Game | Trinity-Pawlin Rink | vs. Northwestern 14U A1 - Open |
| Sunday | November 26, 2023 | 2:30 AM | 4:00 AM | Game | Salisbury | @ Salisbury A |
| Wednesday | November 29, 2023 | 8:15 PM | 9:30 PM | Practice | Trinity Pawlin | |
| Friday | December 1, 2023 | 8:40 PM | 9:50 PM | Practice | Brewster Ice Pond | Pee Wee |
| Saturday | December 2, 2023 | 11:30 AM | 1:00 PM | Game | Trinity-Pawling School | vs. Greenwich Skate A |
| Saturday | December 2, 2023 | 11:30 AM | 12:30 PM | Game | Trinity-Pawlin Rink | @ Greenwich Cardinals 14U - Undeclared |
| Sunday | December 3, 2023 | 4:15 PM | 5:30 PM | Game | Choate Rink | @ Wallingford 14U A - Open |
| Wednesday | December 6, 2023 | 8:15 PM | 9:30 PM | Practice | Trinity Pawlin | |
| Friday | December 8, 2023 | 7:30 PM | 8:40 PM | Practice | Brewster Ice Pond | Pee Wee |
| Saturday | December 9, 2023 | 11:00 AM | 12:30 PM | Game | Trinity-Pawlin Rink | vs. Stamford 14U A1 |
| Wednesday | December 13, 2023 | 8:15 PM | 9:15 PM | Practice | Trinity Pawlin | |
| Friday | December 15, 2023 | 8:40 PM | 9:50 PM | Practice | Brewster Ice Pond | Pee Wee |
| Saturday | December 16, 2023 | 1:00 PM | 2:30 PM | Game | Trinity-Pawling School | vs. Salisbury A |
| Sunday | December 17, 2023 | 10:30 AM | 11:45 AM | Game | Dorothy Hamill Rink | @ Greenwich Cardinals 14U - Undeclared |
| Wednesday | December 20, 2023 | 8:15 PM | 9:15 PM | Practice | Trinity Pawlin | |
| Friday | December 22, 2023 | 8:40 PM | 9:50 PM | Practice | Brewster Ice Pond | Pee Wee |
| Wednesday | December 27, 2023 | 10:30 AM | 11:30 AM | Game | Simsbury Farms Recreation | @ Salisbury Redhawks |
| Thursday | December 28, 2023 | 9:15 AM | 10:15 AM | Game | Simsbury Farms Recreation | @ Simsbury A1 |
| Thursday | December 28, 2023 | 2:15 PM | 3:15 PM | Game | International Skating Center of Connecticut - ISCC | vs. Connecticut Jr Huskies A |
| Friday | December 29, 2023 | 8:00 AM | 9:00 AM | Game | International Skating Center of Connecticut - ISCC | @ Connecticut Jr Huskies A |
| Wednesday | January 3, 2024 | 8:30 PM | 9:30 PM | Practice | Trinity Pawlin | |
| Friday | January 5, 2024 | 8:40 PM | 9:50 PM | Practice | Brewster Ice Pond | Pee Wee |
| Saturday | January 6, 2024 | 10:30 AM | 12:00 PM | Game | Trinity-Pawlin Rink | vs. Central 14U Minor |
| Sunday | January 7, 2024 | 11:40 AM | 1:10 PM | Game | Winter Garden Rink | @ Ridgefield 14U A1 |
| Wednesday | January 10, 2024 | 8:15 PM | 9:30 PM | Practice | Trinity Pawlin | |
| Friday | January 12, 2024 | 8:40 PM | 9:50 PM | Practice | Brewster Ice Pond | Pee Wee |
| Saturday | January 13, 2024 | 11:00 AM | 12:30 PM | Game | Trinity-Pawlin Rink | vs. Pawling 14U B - Open |
| Sunday | January 14, 2024 | 6:00 PM | 7:15 PM | Game | Northford Blue | @ Junior Bulldogs 14U A |
| Wednesday | January 17, 2024 | 8:15 PM | 9:15 PM | Practice | Trinity Pawlin | |
| Friday | January 19, 2024 | 8:40 PM | 9:50 PM | Practice | Brewster Ice Pond | Pee Wee |
| Saturday | January 20, 2024 | 11:00 AM | 12:30 PM | Practice | Trinity Pawlin | |
| Sunday | January 21, 2024 | 1:00 PM | 2:30 PM | Game | Canterbury | @ Northwestern 14U A1 - Open |
| Wednesday | January 24, 2024 | 8:15 PM | 9:30 PM | Practice | Trinity Pawlin | |
| Friday | January 26, 2024 | 8:40 PM | 9:50 PM | Practice | Brewster Ice Pond | Pee Wee |
| Saturday | January 27, 2024 | 10:45 AM | 12:15 PM | Game | Trinity-Pawlin Rink | vs. Greenwich Skating Club 14U A - Open |
| Sunday | January 28, 2024 | 3:40 PM | 5:00 PM | Game | Stamford Twin E | @ Darien 14U B |
| Wednesday | January 31, 2024 | 8:30 PM | 9:30 PM | Practice | Trinity Pawlin | |
| Friday | February 2, 2024 | 8:30 PM | 9:45 PM | Game | GSC | @ Greenwich Skating Club 14U A - Open |
| Saturday | February 3, 2024 | 1:00 PM | 2:30 PM | Game | Trinity-Pawlin Rink | vs. Enfield 14U B |
| Sunday | February 4, 2024 | 11:40 AM | 1:10 PM | Game | Winter Garden Rink | @ Ridgefield 14U A1 |
| Wednesday | February 7, 2024 | 7:00 PM | 8:00 PM | Practice | Trinity Pawlin | Pee Wee |
| Friday | February 9, 2024 | 7:45 PM | 9:15 PM | Practice | Brewster Ice Pond | Pee Wee |
| Saturday | February 10, 2024 | 1:10 PM | 2:40 PM | Game | Champions Upper Rink | @ Central 14U Minor |
| Sunday | February 11, 2024 | 8:00 AM | 9:30 AM | Game | Brewster Ice 1 | vs. Wonderland 14U A - Open |
| Wednesday | February 14, 2024 | 7:45 PM | 9:15 PM | Practice | Trinity Pawlin | Pee Wee |
| Friday | February 16, 2024 | 8:40 PM | 9:50 PM | Practice | Brewster Ice Pond | Pee Wee |
| Saturday | February 17, 2024 | 10:30 AM | 12:00 PM | Game | Trinity-Pawlin Rink | vs. Watertown 14U A |
| Wednesday | February 21, 2024 | 8:15 PM | 9:30 PM | Practice | Trinity Pawlin | Midget |
| Friday | February 23, 2024 | 5:00 PM | 6:30 PM | Game | Northford | @ Mid Fairfield |
| Saturday | February 24, 2024 | 12:30 PM | 2:00 PM | Game | Northford Ice Pavilion | @ West Hartford A |
| Saturday | February 24, 2024 | 7:30 PM | 9:00 PM | Game | Northford Ice Pavilion | @ CT JR Huskies A |
| Wednesday | February 28, 2024 | 7:00 PM | 8:00 PM | Practice | Trinity Pawlin | Midget |
| Friday | March 1, 2024 | 7:30 PM | 9:00 PM | Practice | Trinity Pawlin | Midget Fall |
| Wednesday | March 6, 2024 | 8:15 PM | 9:30 PM | Practice | Trinity Pawlin | Midget |