| December 1, 3:30 pm | Boys Junior Varsity Basketball vs. Covenant Christian | Landmark: 29 CC: 30 |
| December 5, 3:45 pm | Boys Junior Varsity Basketball @ Cambridge School of Weston | Landmark: 21 CSW: 35 |
| December 7, 4:00 pm | Boys Junior Varsity Basketball vs. Concord Academy | Landmark: 21 Concord: 27 |
| December 8, 3:30 pm | Boys Junior Varsity Basketball vs. Pingree | |
| December 13, 4:00 pm | Boys Junior Varsity Basketball vs. LCA | |
| December 15, 4:00 pm | Boys Junior Varsity Basketball @ Gann Academy | |
| January 4, 3:45 pm | Boys Junior Varsity Basketball @ Dexter Southfield | |
| January 11, 3:45 pm | Boys Junior Varsity Basketball vs. Berwick Academy | |
| January 18, 4:15 pm | Boys Junior Varsity Basketball vs. Bancroft | |
| January 20, 4:00 pm | Boys Junior Varsity Basketball @ Portsmouth Abbey | |
| January 25, 4:30 pm | Boys Junior Varsity Basketball @ Berwick Academy | |
| January 30, 4:00 pm | Boys Junior Varsity Basketball vs. Pingree | |
| February 1, 3:45 pm | Boys Junior Varsity Basketball @ Bancroft | |
| February 3, 4:00 pm | Boys Junior Varsity Basketball @ LCA | |
| February 8, 4:00 pm | Boys Junior Varsity Basketball vs. Beaver Country Day | |
| February 10, 3:45 pm | Boys Junior Varsity Basketball vs. Chapel Hill CANCELLED | CANCELLED |
| February 13, 4:00 pm | Boys Junior Varsity Basketball @ Beaver Country Day | |
| February 15, 4:00 pm | Boys Junior Varsity Basketball vs. Portsmouth Abbey | |
| February 22, 3:45 pm | Boys Junior Varsity Basketball @ Concord Academy | |
