| Day | Date | From | To | Type | Location | Opponent / Sharing With |
|---|---|---|---|---|---|---|
| Tuesday | August 8, 2023 | 10:30 AM | 12:00 PM | Practice | Brewster Ice 98 | Midget |
| Friday | August 18, 2023 | 7:50 PM | 9:10 PM | Practice | Brewster Ice 98 | Midget |
| Sunday | August 20, 2023 | 9:45 AM | 11:00 AM | Game | HAR | @ Bedford |
| Wednesday | August 30, 2023 | 8:20 PM | 9:20 PM | Practice | Brewster Ice 98 | Midget |
| Saturday | September 2, 2023 | 6:55 PM | 8:25 PM | Game | Stamford Twin E | @ Darien 16U White |
| Wednesday | September 6, 2023 | 5:00 PM | 7:00 PM | Training | Tarrywile Park | |
| Friday | September 8, 2023 | 8:50 PM | 9:50 PM | Practice | Brewster Ice 98 | Midget |
| Sunday | September 10, 2023 | 8:00 PM | 9:20 PM | Game | Brewster Ice 1 | vs. Greenwich Cardinals 16U - Undeclared |
| Friday | September 15, 2023 | 7:10 PM | 8:10 PM | Practice | Brewster Ice 99 | Midget |
| Saturday | September 16, 2023 | 4:30 PM | 6:30 PM | Game | ISCC NHL | @ Simsbury 16U - Undeclared |
| Friday | September 22, 2023 | 8:50 PM | 9:50 PM | Practice | Brewster Ice 98 | Midget |
| Sunday | September 24, 2023 | 1:30 PM | 3:00 PM | Game | Trinity-Pawlin Rink | vs. Central 16U American |
| Sunday | September 24, 2023 | 8:00 PM | 9:00 PM | Game | Brewster Ice Arena | vs. TBD |
| Tuesday | September 26, 2023 | 7:15 PM | 8:15 PM | Practice | Trinity Pawlin | |
| Friday | September 29, 2023 | 7:10 PM | 8:10 PM | Practice | Brewster Ice 99 | Midget |
| Saturday | September 30, 2023 | 12:15 PM | 1:45 PM | Game | Trinity-Pawlin Rink | vs. Northwestern 18U - Undeclared |
| Sunday | October 1, 2023 | 2:00 PM | 3:00 PM | Game | ISCC NHL | @ Simsbury 16U - Undeclared |
| Wednesday | October 4, 2023 | 8:30 PM | 9:30 PM | Practice | Trinity Pawlin | Midget |
| Saturday | October 7, 2023 | 4:00 PM | 5:20 PM | Game | Milford Ice Rink | @ Southern 18U Milford - Undeclared |
| Wednesday | October 11, 2023 | 8:30 PM | 9:30 PM | Practice | Trinity Pawlin | Midget |
| Friday | October 13, 2023 | 7:10 PM | 8:10 PM | Practice | Brewster Ice 99 | Midget |
| Saturday | October 14, 2023 | 3:15 PM | 4:45 PM | Game | Trinity-Pawlin Rink | vs. Simsbury 16U - Undeclared |
| Sunday | October 15, 2023 | 6:55 PM | 8:15 PM | Game | Wonderland Stadium | @ Wonderland 16U White Open |
| Wednesday | October 18, 2023 | 8:30 PM | 9:30 PM | Practice | Trinity Pawlin | Midget |
| Saturday | October 21, 2023 | 7:15 PM | 8:30 PM | Game | Dorothy Hamill Skating Rink | @ GREENWICH CARDINALS |
| Sunday | October 22, 2023 | 12:30 PM | 1:50 PM | Game | Brewster Ice 1 | vs. CT RiverHawks 18U - THS |
| Wednesday | October 25, 2023 | 8:30 PM | 9:30 PM | Practice | Trinity Pawlin | Midget |
| Friday | October 27, 2023 | 7:10 PM | 8:10 PM | Practice | Brewster Ice 99 | Midget |
| Saturday | October 28, 2023 | 12:15 PM | 1:45 PM | Game | Trinity-Pawlin Rink | vs. Darien 16U White |
| Wednesday | November 1, 2023 | 8:30 PM | 9:30 PM | Practice | Trinity Pawlin | Midget |
| Saturday | November 4, 2023 | 8:30 PM | 10:00 PM | Game | Shelton Lower | @ CT RiverHawks 18U - THS |
| Sunday | November 5, 2023 | 1:45 PM | 3:15 PM | Game | Trinity-Pawlin Rink | vs. Southern 18U Milford - Undeclared |
| Wednesday | November 8, 2023 | 8:30 PM | 9:30 PM | Practice | Trinity Pawlin | Midget |
| Friday | November 10, 2023 | 7:10 PM | 8:10 PM | Practice | Brewster Ice 99 | Midget |
| Saturday | November 11, 2023 | 2:00 PM | 3:30 PM | Game | Choate Rink | @ Wallingford 18U - Undeclared |
| Sunday | November 12, 2023 | 10:30 AM | 12:00 PM | Game | Dorothy Hamill Rink | @ Greenwich Cardinals 16U - Undeclared |
| Wednesday | November 15, 2023 | 8:30 PM | 9:30 PM | Practice | Trinity Pawlin | Midget |
| Sunday | November 19, 2023 | 6:10 PM | 7:40 PM | Game | Terry Conners Rink | @ Stamford 18U A1 - Undeclared |
| Friday | March 1, 2024 | 7:30 PM | 9:00 PM | Practice | Trinity Pawlin | Bantam |