| 11/08/1986 | | ISAA Championship |
| 11/08/1986 | | IAC Championship |
| 11/08/1986 | | Maryland State Championship |
| 10/31/1986 | | MCPS Division Champions |
| 10/30/1986 | | Class AA Region I |
| 10/30/1986 | | Class A Region I |
| 10/30/1986 | | Class B Region I |
| 10/29/1986 | | Class AA Region II |
| 10/25/1986 | | Metro Catholic Championships |
| 10/24/1986 | | Montgomery Co. XC Championship |
| 10/22/1986 | | WJ at Woodward |
| 10/22/1986 | | Magruder at Churchill |
| 10/22/1986 | | Damascus, Sherwood at RM |
| 10/22/1986 | | PB, Wheaton at Wootton |
| 10/22/1986 | | Kennedy, Einstein at B-CC |
| 10/22/1986 | | Seneca Valley, Blair at Rockville |
| 10/22/1986 | | Whitman, Gburg at Springbrook |
| 10/18/1986 | | Georgetown Prep Classic |
| 10/15/1986 | | Magruder, Woodward at RM |
| 10/15/1986 | | Wootton at Kennedy |
| 10/15/1986 | | Gaithersburg at Rockville |
| 10/15/1986 | | GC, HC at Sherwood |
| 10/15/1986 | | Einstein at Wheaton |
| 10/15/1986 | | B-CC at Paint Branch |
| 10/15/1986 | | Seneca Valley at Springbrook |
| 10/11/1986 | | Hereford Invitational |
| 10/07/1986 | | B-CC at Wootton |
| 10/07/1986 | | Whitman at Rockville |
| 10/07/1986 | | Springbrook at Blair |
| 10/07/1986 | | Churchill, Gburg at SV |
| 10/07/1986 | | Woodward at Sherwood |
| 10/07/1986 | | Damascus at Magruder |
| 10/07/1986 | | DeMatha, PB at Einstein |
| 10/07/1986 | | Kennedy at Wheaton |
| 10/02/1986 | | RM, Good Counsel at Einstein |
| 09/30/1986 | | Seneca Valley at Whitman |
| 09/30/1986 | | Wheaton at B-CC |
| 09/30/1986 | | Paint Branch at Kennedy |
| 09/30/1986 | | Damascus at Woodward |
| 09/30/1986 | | Sherwood, WJ at Magruder |
| 09/27/1986 | | Arundel Invitational |
| 09/27/1986 | | Pallotti Invitational |
| 09/20/1986 | | Spiked Shoe Invitational |
| 09/10/1986 | | Landon vs. Bullis |
| 09/09/1986 | | Woodward Relays |
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