| 11/27/1999 | | Footlocker Northeast Regional |
| 11/13/1999 | | IAC/ISL Championship |
| 11/13/1999 | | WCAC Championship |
| 11/13/1999 | | MD XC State Championship |
| 11/05/1999 | | Madeira Invitational |
| 11/04/1999 | | 4A West Regional |
| 11/04/1999 | | 1A Central Regional |
| 11/04/1999 | | 3A West Regional |
| 11/04/1999 | | 2A West Regional |
| 11/01/1999 | | Washington Cross Country Report 6 |
| 10/31/1999 | | MCPS Division Champions |
| 10/31/1999 | | Mid-Atlantic Private Invitational |
| 10/28/1999 | | Montgomery Co. XC Championship |
| 10/26/1999 | | Private School Meet |
| 10/23/1999 | | Octoberfest Invitational |
| 10/22/1999 | | Ireton, Gonzaga, Holton, Episcopal |
| 10/21/1999 | | Knights Invitational |
| 10/19/1999 | | 5 Team Meet |
| 10/16/1999 | | Eastern States Championship |
| 10/16/1999 | | Georgetown Prep Classic |
| 10/13/1999 | | PVAC Championship |
| 10/12/1999 | | Poolesville vs. Blair |
| 10/12/1999 | | Washington Cross Country Report 4 |
| 10/12/1999 | | Magruder at Seneca Valley |
| 10/12/1999 | | Gaithersburg at Quince Orchard |
| 10/09/1999 | | Lancer Invitational |
| 10/09/1999 | | Manhattan Invitational |
| 10/09/1999 | | Glory Days Invitational |
| 10/06/1999 | | Northwest Quad Meet |
| 10/06/1999 | | GP XC Quad Meet |
| 10/06/1999 | | SV Quad Meet |
| 10/06/1999 | | Wheaton Quad Meet |
| 10/05/1999 | | Glenelg Country Meet |
| 10/05/1999 | | Quince Orchard Quad |
| 10/02/1999 | | Mercersburg Invitational |
| 10/02/1999 | | Salesianum Invitational |
| 10/02/1999 | | William and Mary Invitational |
| 09/29/1999 | | Magruder, RM at Springbrook |
| 09/29/1999 | | Landon, WF at GP |
| 09/28/1999 | | Ireton, Bullis |
| 09/28/1999 | | WJ, WW, Churchill @ Gburg |
| 09/25/1999 | | Brunswick Invitational |
| 09/24/1999 | | Bull Run Invitational |
| 09/22/1999 | | Einstein vs. Blair |
| 09/22/1999 | | Churchill, Springbrook, Wheaton |
| 09/21/1999 | | St. Andrew's, Bullis |
| 09/21/1999 | | Private School Meet |
| 09/21/1999 | | Northwest, Blake, Blair |
| 09/18/1999 | | Virginia Tech Invitational |
| 09/18/1999 | | Spiked Shoe at Penn State |
| 09/12/1999 | | Washington Cross Country Report 2 |
| 09/11/1999 | | Peter Geraghty Invitational |
| 09/09/1999 | | Private School Meet |
| 09/05/1999 | | Woodward Relays |
