| Mon, 12/4/23 to Sun, 12/10/23Week 2 |
| Friday, December 8, 2023 |
| 8:40 pm | Middle School Boys | 6L | vs. | Hanover | 7W | Bog |
| Saturday, December 9, 2023 |
| 12:00 pm | Freshman Boys Hockey | 7W | vs. | Marshfield JV2 | 5L | Armstrong |
| Sunday, December 10, 2023 |
| 5:30 pm | Freshman Boys Hockey | 9W | vs. | Cohassett JV | 1L | Hobomock Arena |
| 6:50 pm | JV Boys Hockey | 3W | vs. | Scituate JV | 1L | Bog |
| Mon, 12/11/23 to Sun, 12/17/23Week 3 |
| Wednesday, December 13, 2023 |
| 7:10 pm | St Marys Lynn | 4L | vs. | Varsity Boys Hockey | 7W | Canton Sportsplex |
| Friday, December 15, 2023 |
| 7:00 pm | Middle School Boys | 2T | vs. | Braintree | 2T | Bog |
| Saturday, December 16, 2023 |
| 7:40 pm | Bishop Feehan | 0L | vs. | Varsity Boys Hockey | 8W | Canton Sportsplex |
| Sunday, December 17, 2023 |
| 5:30 pm | Freshman Boys Hockey | 6W | vs. | Abington JV | 4L | Hobomock Arena |
| 5:40 pm | JV Boys Hockey | 7W | vs. | Weymouth JV | 0L | Bog |
| Mon, 12/18/23 to Sun, 12/24/23Week 4 |
| Wednesday, December 20, 2023 |
| 5:10 pm | Xaverian Freshman | 3W | vs. | JV Boys Hockey | 1L | Canton Sportsplex |
| 8:00 pm | Varsity Boys Hockey | 3W | vs. | Arlington Catholic | 1L | Veterans (Ed Burns Arena) |
| Saturday, December 23, 2023 |
| 7:40 pm | Central Catholic | 1L | vs. | Varsity Boys Hockey | 4W | Canton Sportsplex |
| Mon, 12/25/23 to Sun, 12/31/23Week 5 |
| Tuesday, December 26, 2023 |
| 8:40 am | JV Boys Hockey | 5W | vs. | Waltham JV | 1L | Watertown Rink (John A. Ryan) |
| Wednesday, December 27, 2023 |
| 9:50 am | Freshman Boys Hockey | 2L | vs. | St. Mary's JV | 6W | Watertown Rink (John A. Ryan) |
| 4:00 pm | Varsity Boys Hockey | 3L | vs. | Arrow Holiday Classic - Xaverian | 4W | Randolph |
| 5:10 pm | St. John’s Shrewsbury JV | 3T | vs. | JV Boys Hockey | 3T | Canton Sportsplex |
| Friday, December 29, 2023 |
| 8:40 am | JV Boys Hockey | 5W | vs. | Arlington Catholic JV | 4L | Watertown Rink (John A. Ryan) |
| 4:00 pm | Varsity Boys Hockey | 5W | vs. | Arrow Holiday Classic - Braintree | 1L | Randolph |
| Sunday, December 31, 2023 |
| 10:10 am | JV Boys Hockey | 9W | vs. | BC High JV1 | 0L | Bog |
| 1:10 pm | Freshman Boys Hockey | 4W | vs. | SSVT JV | 0L | Hobomock Arena |
| Mon, 1/1/24 to Sun, 1/7/24Week 6 |
| Wednesday, January 3, 2024 |
| 5:10 pm | Walpole JV2 | 0L | vs. | Freshman Boys Hockey | 4W | Canton Sportsplex |
| Friday, January 5, 2024 |
| 5:40 pm | Middle School Boys | 3T | vs. | Norwell | 3T | Hobomock Arena |
| Saturday, January 6, 2024 |
| 6:00 pm | Varsity Boys Hockey | 10W | vs. | Bishop Fenwick | 2L | McVan/O'Keefe Memorial Arena |
| 7:40 pm | Xaverian JV | 8W | vs. | JV Boys Hockey | 1L | Canton Sportsplex |
| Sunday, January 7, 2024 |
| 2:00 pm | Freshman Boys Hockey | 11W | vs. | Duxbury JV2 | 2L | Hobomock Arena |
| 6:50 pm | JV Boys Hockey | 0L | vs. | Duxbury JV | 2W | Bog |
| Mon, 1/8/24 to Sun, 1/14/24Week 7 |
| Wednesday, January 10, 2024 |
| 8:00 pm | Varsity Boys Hockey | 4W | vs. | St Marys Lynn | 0L | Connery Rink |
| Friday, January 12, 2024 |
| 8:10 pm | Middle School Boys | 4L | vs. | Marshfield | 5W | Bog |
| Saturday, January 13, 2024 |
| 7:40 pm | Needham | 3L | vs. | Varsity Boys Hockey | 7W | Canton Sportsplex |
| Sunday, January 14, 2024 |
| 3:40 pm | JV Boys Hockey | 6W | vs. | BC High JV2 | 1L | Hobomock Arena |
| 3:50 pm | Freshman Boys Hockey | 1L | vs. | Norwell JV | 2W | Hobomock Arena |
| Mon, 1/15/24 to Sun, 1/21/24Week 8 |
| Monday, January 15, 2024 |
| 3:00 pm | Varsity Boys Hockey | 5W | vs. | Milton | 4L | Ulin Ice Arena (Milton) |
| Wednesday, January 17, 2024 |
| 3:00 pm | Freshman Boys Hockey | 12W | vs. | Hingham JV2 | 4L | Connell Memorial Rink |
| 5:00 pm | Varsity Boys Hockey | 4W | vs. | Canton | 3L | Ponkapoag (Canton) |
| 5:10 pm | Canton JV | 3W | vs. | JV Boys Hockey | 1L | Canton Sportsplex |
| Friday, January 19, 2024 |
| 7:00 pm | Middle School Boys | 2L | vs. | Pembroke | 5W | Bog |
| Saturday, January 20, 2024 |
| 5:40 pm | Canton JV2 | 6W | vs. | Freshman Boys Hockey | 2L | Canton Sportsplex |
| 6:00 pm | JV Boys Hockey | 1L | vs. | Xaverian JV | 3W | Milton Academy |
| 6:30 pm | Varsity Boys Hockey | 6W | vs. | Bishop Feehan | 1L | New England Sports Village |
| Sunday, January 21, 2024 |
| 3:20 pm | JV Boys Hockey | 8W | vs. | Braintree JV | 1L | Bog |
| 5:30 pm | Freshman Boys Hockey | 4W | vs. | Pembroke JV | 3L | Hobomock Arena |
| Mon, 1/22/24 to Sun, 1/28/24Week 9 |
| Wednesday, January 24, 2024 |
| 3:00 pm | JV Boys Hockey | 5T | vs. | Hingham JV1 | 5T | Connell Memorial Rink |
| 7:10 pm | Arlington Catholic | 1L | vs. | Varsity Boys Hockey | 2W | Canton Sportsplex |
| Friday, January 26, 2024 |
| —:— — | Middle School Boys | | vs. | TBA | | Bog |
| Saturday, January 27, 2024 |
| 12:00 pm | JV Boys Hockey | 1L | vs. | Pope Francis JV | 4W | Olympia Rink |
| 2:00 pm | Varsity Boys Hockey | 4L | vs. | Pope Francis | 5W | Olympia Rink |
| Sunday, January 28, 2024 |
| 2:00 pm | Freshman Boys Hockey | 5W | vs. | Marshfield JV2 | 3L | Hobomock Arena |
| 6:50 pm | JV Boys Hockey | 3W | vs. | Marshfield JV1 | 2L | Bog |
| Mon, 1/29/24 to Sun, 2/4/24Week 10 |
| Wednesday, January 31, 2024 |
| 7:10 pm | St. Johns Prep Freshman | 3L | vs. | JV Boys Hockey | 5W | Canton Sportsplex |
| Thursday, February 1, 2024 |
| 6:30 pm | Freshman Boys Hockey | 5W | vs. | BC High Freshman | 1L | UMASS - Boston |
| Friday, February 2, 2024 |
| 7:30 pm | Middle School Boys | | vs. | Marshfield | | Bog |
| Saturday, February 3, 2024 |
| 7:40 pm | Bishop Fenwick | 0L | vs. | Varsity Boys Hockey | 10W | Canton Sportsplex |
| Sunday, February 4, 2024 |
| 4:30 pm | JV Boys Hockey | 6W | vs. | Plymouth North JV | 0L | Bog |
| 6:40 pm | Freshman Boys Hockey | 4W | vs. | Hingham JV2 | 3L | Hobomock Arena |
| Mon, 2/5/24 to Sun, 2/11/24Week 11 |
| Wednesday, February 7, 2024 |
| 3:10 pm | Catholic Memorial | 3W | vs. | Varsity Boys Hockey | 2L | Canton Sportsplex |
| Friday, February 9, 2024 |
| 7:30 pm | Middle School Boys | | vs. | Norwell | | Bog |
| Saturday, February 10, 2024 |
| 10:00 am | Freshman Boys Hockey | | vs. | Xaverian Freshman | | Milton Academy |
| 4:30 pm | JV Boys Hockey | | vs. | St. Johns Prep Freshman | | Essex Ice Arena |
| 7:40 pm | Exeter, NH | 3L | vs. | Varsity Boys Hockey | 8W | Canton Sportsplex |
| Sunday, February 11, 2024 |
| 2:00 pm | Freshman Boys Hockey | | vs. | Whitman Hanson JV | | Hobomock Arena |
| 3:20 pm | JV Boys Hockey | | vs. | Silver Lake JV | | Bog |
| Mon, 2/12/24 to Sun, 2/18/24Week 12 |
| Wednesday, February 14, 2024 |
| 5:10 pm | Franklin | 7W | vs. | Varsity Boys Hockey | 2L | Canton Sportsplex |
| Saturday, February 17, 2024 |
| —:— — | Varsity Boys Hockey | 6W | vs. | Buddy Ferreira Classic | 2L | Falmouth Arena |
| Sunday, February 18, 2024 |
| —:— — | Varsity Boys Hockey | 3W | vs. | Buddy Ferreira Classic | 2L | Falmouth Arena |
| 5:30 pm | Freshman Boys Hockey | | vs. | Cohassett JV | | Hobomock Arena |
| 6:50 pm | JV Boys Hockey | | vs. | Scituate JV | | Bog |
| Mon, 2/19/24 to Sun, 2/25/24Week 13 |
| Monday, February 19, 2024 |
| —:— — | Freshman Boys Hockey | | vs. | JV2 League Championship | | Bog |
| —:— — | JV Boys Hockey | | vs. | JV League Championship | | Bog |
| Wednesday, February 21, 2024 |
| —:— — | Varsity Boys Hockey | 2W | vs. | Buddy Ferreira Classic | 1L | Falmouth Arena |
| Friday, February 23, 2024 |
| 7:00 pm | Middle School Boys | | vs. | Pembroke | | Bog |
