| Tue, Sep 4 | Woodward Cross-country Relays | Georgetown Prep | North Bethesda, MD | 3:30 PM | | |
| Tue, Sep 11 | MCPS Wootton at B-CC | Candy Cane City | Chevy Chase, MD | 3:30 PM | | |
| Tue, Sep 18 | Churchill at Wootton | Thomas Wootton HS | Rockville, MD | | | |
| Sat, Sep 22 | Oatlands Invitational | Oatlands Plantation | Leesburg, VA | | | |
| Sat, Sep 29 | Carlisle Invitational | Carlisle | Carlisle, PA | 9:15 AM | | |
| Tue, Oct 2 | Quince Orchard @ Wootton | Thomas Wootton HS | Rockville, MD | | | |
| Tue, Oct 9 | Whitman & Wooton vs. Sherwood | Sherwood HS | Sandy Spring, MD | 3:30 PM | | |
| Sat, Oct 20 | Montgomery County Championships | Gaithersburg HS | Gaithersburg, MD | 9:00 AM | | |
| Thu, Nov 1 | MPSSAA 4A/3A West Regional Championships | High Point Farm | Clarksburg, MD | | | |
| Sat, Nov 10 | MPSSAA Maryland State Championship | Hereford HS | Parkton, MD | | | |
