| Sat, Aug 27 | Team Time Trial and Potluck Picnic 11:00 AM | Damascus | Damascus, MD | | | |
| Fri, Sep 9 | Magruder Invitational (Cancelled) | Agricultural Farm Park | Derwood, MD | 3:45 PM | | |
| Tue, Sep 20 | Whitman, Damascus @ Magruder | Lake Needwood Regional Park | Rockville, MD | 3:30 PM | | |
| Sat, Sep 24 | Bull Run Invitational | Hereford HS | Parkton, MD | | | |
| Tue, Sep 27 | Tri meet B-CC & RM @ Damascus | Damascus | Damascus, MD | | | |
| Fri, Sep 30 | Paul Short Invitational | Lehigh University-Goodman Campus | Bethlehem, PA | 3:15 PM | | |
| Tue, Oct 4 | Walt Whitman & Damascus vs. Magruder | Lake Needwood Regional Park | Rockville, MD | | | |
| Thu, Oct 6 | Oakdale Invitational | Libertytown Park | Libertytown, MD | 4:00 PM | | |
| Sat, Oct 15 | Georgetown Prep Cross-Country Classic | Georgetown Prep | North Bethesda, MD | 12:45 PM | | |
| Sat, Oct 22 | Montgomery County Championships | Gaithersburg HS | Gaithersburg, MD | 9:00 AM | | |
| Thu, Nov 3 | MPSSAA 3A West Regional Championship | Governor Thomas Johnson HS | Frederick, MD | | | |
| Sat, Nov 12 | Maryland State Championships | Hereford HS | Parkton, MD | 10:00 AM | | |
