| Fri, Sep 10 | Magruder Invitational | Agricultural Farm Park | Derwood, MD | 3:45 PM | | |
| Wed, Sep 15 | Churchill at Wootton | Thomas Wootton HS | Rockville, MD | | | |
| Tue, Sep 21 | Wootton at Northwest | Northwest HS | Germantown, MD | | | |
| Sat, Sep 25 | Bull Run Invitational | Hereford HS | Parkton, MD | 9:00 AM | | |
| Tue, Oct 5 | Walt Whitman & Wootton vs. Walter Johnson | Cabin John Park | Bethesda, MD | | | |
| Sat, Oct 16 | Fall Classic at Georgetown Prep | Georgetown Prep | North Bethesda, MD | 12:45 PM | | |
| Sat, Oct 23 | Montgomery County Championships | Gaithersburg HS | Gaithersburg, MD | 9:10 AM | | |
| Thu, Nov 4 | MPSSAA 3A/4A West Regional Championships | Watkins Mill HS | Gaithersburg, MD | 3:00 PM | | |
| Sat, Nov 13 | MPSSAA State Cross Country Championships | Hereford HS | Parkton, MD | 10:00 AM | | |
