| December 4, 4:45 | Boys MS Varsity Basketball vs. Cape Ann Waldorf | |
| December 7, 3:30 | Boys MS Varsity Basketball vs. Lexington Christian Academy | |
| December 11, 4:45 | Boys MS Varsity Basketball vs. Covenant Christian Academy | |
| January 10, 4:30 | Boys MS Varsity Basketball @ Glen Urquhart | |
| January 15, 4:30 | Boys MS Varsity Basketball vs. Carroll School | |
| January 17, 4:30 | Boys MS Varsity Basketball @ Tower School | |
| January 24, 4:30 | Boys MS Varsity Basketball @ Carroll School | |
| January 28, 3:30 | Boys MS Varsity Basketball @ Brookwood | |
| January 31, 4:30 | Boys MS Varsity Basketball @ Lexington Christian Academy | |
| February 6, 3:30 | Boys MS Varsity Basketball vs. Glen Urquhart | |
| February 7, 3:30 | Boys MS Varsity Basketball vs. Tower School | |
| February 12, 3:30 | *Postponed from 2/11* Boys MS Varsity Basketball vs. Cape Ann Waldorf | |
| February 13, 3:30 | Boys MS Varsity Basketball vs. Brookwood | |
| April 30, 3:45 | Boys Middle School Baseball @ Lexington Christian Academy | |
