| Day | Date | From | To | Type | Location | Opponent / Sharing With |
|---|---|---|---|---|---|---|
| Wednesday | August 25, 2021 | 5:45 PM | 9:00 PM | Training | O'Brien Rink | |
| Thursday | August 26, 2021 | 5:45 PM | 9:00 PM | Training | O'Brien Rink | |
| Tuesday | August 31, 2021 | 8:00 PM | 9:00 PM | Practice | O'Brien | |
| Thursday | September 9, 2021 | 9:00 PM | 9:50 PM | Practice | O'Brien | |
| Saturday | September 11, 2021 | 11:40 AM | 1:10 PM | Game | Stoneham Arena | vs. Melrose U18 |
| Thursday | September 16, 2021 | 9:00 PM | 9:50 PM | Practice | O'Brien | |
| Sunday | September 19, 2021 | 9:20 AM | 10:50 AM | Game | Stoneham Arena | vs. Stoneham Spartans U18 A |
| Thursday | September 23, 2021 | 9:00 PM | 9:50 PM | Practice | O'Brien | |
| Saturday | September 25, 2021 | 5:30 PM | 6:30 PM | Game | Woburn O'Brien Rink | vs. Wakefield Warriors U18 |
| Thursday | September 30, 2021 | 9:00 PM | 9:50 PM | Practice | O'Brien | |
| Saturday | October 2, 2021 | 4:20 PM | 5:20 PM | Game | Woburn O'Brien Rink | vs. Junior Crusaders U18 |
| Thursday | October 7, 2021 | 9:00 PM | 9:50 PM | Practice | O'Brien | |
| Sunday | October 10, 2021 | 5:10 PM | 6:10 PM | Game | Stoneham Arena | vs. Pingree Highlanders U18 |
| Thursday | October 14, 2021 | 9:00 PM | 9:50 PM | Practice | O'Brien | |
| Sunday | October 17, 2021 | 3:00 PM | 4:00 PM | Game | Watertown Ryan Arena | vs. Norwood Nuggets U18 |
| Thursday | October 21, 2021 | 9:00 PM | 9:50 PM | Practice | O'Brien | |
| Thursday | October 28, 2021 | 9:00 PM | 9:50 PM | Practice | O'Brien | |
| Sunday | October 31, 2021 | 9:20 AM | 10:20 AM | Game | Woburn O'Brien Rink | vs. Lady Lancers U16 Blue |
| Thursday | November 4, 2021 | 9:00 PM | 9:50 PM | Practice | O'Brien | |
| Sunday | November 7, 2021 | 9:20 AM | 10:20 AM | Game | Middleton Essex Sports Center | vs. Pingree Highlanders U18 |
| Thursday | November 11, 2021 | 9:00 PM | 9:50 PM | Practice | O'Brien | |
| Thursday | November 18, 2021 | 9:00 PM | 9:50 PM | Practice | O'Brien | |
| Saturday | November 20, 2021 | 5:30 PM | 6:30 PM | Game | Woburn O'Brien Rink | vs. Junior Crusaders U18 |
| Sunday | November 21, 2021 | 9:50 AM | 10:50 AM | Game | Stoneham Arena | vs. Lady Lancers U16 Blue |
| Sunday | December 12, 2021 | 6:00 PM | 10:00 PM | Other | South End Italian Club | |
| Wednesday | March 2, 2022 | 8:00 PM | 8:50 PM | Other | O'Brien Rink |