| December 1, 3:45 pm | | Boys MS Varsity Basketball vs. Covenant Christian | |
| December 8, 4:45 pm | | Boys MS Varsity Basketball vs. Cape Ann Waldorf | |
| December 14, 3:30 pm | | Boys MS Varsity Basketball vs. Stoneridge Childrens Montessori | |
| January 5, 3:30 am | | Boys Middle School Basketball @ Carroll School | |
| January 9, 3:30 pm | | Boys Middle School Basketball @ LCA | |
| January 12, 3:30 pm | | Boys Middle School Basketball @ Glen Urquhart | |
| January 17, 3:45 pm | | Boys Middle School Basketball @ Carroll School | |
| January 19, 3:30 pm | | Boys Middle School JV Basketball @ Tower School | |
| January 23, 3:30 pm | | Boys Middle School Basketball vs Landmark JV2 | |
| January 24, 3:30 pm | | Boys Middle School Basketball vs. Cape Ann Waldorf | |
| January 26, 4:30 pm | | Boys Middle School Basketball vs. Carroll School | |
| January 31, 4:30 pm | | Boys Middle School Basketball vs Brookwood | |
| February 2, 5:00 pm | | Boys Middle School Basketball vs. LCA | |
| February 7, 3:30 pm | | Boys Middle School Basketball vs. Shore Country Day (ANSARA HS CAMPUS) | Game at Ansara Center |
| February 8, 3:45 pm | | Boys Middle School V Basketball vs. Tower School | |
| February 9, 4:45 pm | | Boys Middle School JV Basketball vs. Tower School | |
| February 14, 3:30 pm | | Boys Middle School Basketball JV vs Carroll | |
| February 15, 3:30 pm | | Boys Middle School Basketball vs. Glen Urquhart | |
| February 16, 3:00 pm | | Boys Middle School Basketball @ Brookwood | |
