| Day: | Date: | Home Team: | Opponent: | Time: | Score: |
| Fri. | August 25, 2000 | Stone Bridge High School | Potomac School | 7:30 p.m. | 20-23 |
| Sat | August 26, 2000 | Massanutten Military Academy | Roanoke Catholic | 2:00 p.m. | |
| Thuu | August 31, 2000 | Nansemond-Suffolk Academy | Mt. Zion Christian | 7:30 p.m. | 6-36 |
| Fri. | September 1, 2000 | Colonial Beach High School | George Mason | 7:30 p.m. | 6-53 |
| Pallotti High School | Potomac School | 7:30 p.m. | 12-32 | ||
| Greenbrier Christian Academy | Isle of Wight Academy | 7:30 p.m. | 14-0 | ||
| Lynchburg Christian Academy | Atlantic Shores Christian | 7:30 p.m. | 20-8 | ||
| Sat. | September 2, 2000 | Christchurch School | Randolph-Macon Acaemy | 12:00 p.m. | |
| Fri. | September 8, 2000 | Hampton Roads Academy | Broadwater Academy | 7:00 p.m. | |
| Greenbrier Christian Academy | Benedictine High School | 7:30 p.m. | 13-46 | ||
| Fuqua School | Virginia Episcopal School | 7:30 p.m. | 0-34 | ||
| Lynchburg Christian Academy | Hargrave Military Academy | 7:30 p.m. | 12-37 | ||
| Massanutten Military Academy | Brunswick Academy | 4:00 p.m. | 6-27 | ||
| Nansemond-Suffolk Academy | Windsor High School | 7:30 p.m. | 22-6 | ||
| Sat. | September 9, 2000 | Christchurch School | Potomac School | 3:00 p.m. | 9-41 |
| Sidwell Friends | St. Anne's-Belfield | 2:00 p.m. | 21-15 | ||
| Fri. | September 15, 2000 | Hampton Roads Academy | Blue Ridge School | 7:00 p.m. | 3-14 |
| Greenbriar Christian Academy | Christchurch School | 7:00 p.m. | 16-14 | ||
| Lynchburg Christian Academy | Fuqua School | 7:30 p.m. | |||
| Fishburne Military Academy | Massanutten Military Academy | 3:30 p.m. | 14-30 | ||
| Sat. | September 16, 2000 | St. Anne's-Belfield | North Cross | 2:00 p.m. | 24-0 |
| Potomac School | Bishop Ireton High School | 2:00 p.m. | 18-34 | ||
| Virginia Episcopal School | Roanoke Catholic | 2:00 p.m. | |||
| Atlantic Shores Christian | Nansemond-Suffolk Academy | 2:00 p.m. | 0-21 | ||
| Fri. | September 22, 2000 | St. Anne's-Belfield | Potomac School | 7:30 p.m. | 14-21 |
| Blessed Sacrament- Huguenot | Greenbrier Christian Academy | 7:30 p.m. | 7-27 | ||
| Lift Academy | Lynchburg Christian Academy | 7:30 p.m. | 50-0 | ||
| Sat. | September 23, 2000 | Christchurch School | Hampton Roads Academy | 3:00 p.m. | 20-0 |
| Catholic High School | Nansemond-Suffolk Academy | 1:30 p.m. | 0-27 | ||
| Massanutten Military | Colonial Beach High School | 1:30 PM | 47-0 | ||
| Thu | September 28, 2000 | Potomac School | St. James School | 4:30 p.m. | 63-8 |
| Norfolk Academy | Greenbrier Christian Academy | 4:00 p.m. | 26-0 | ||
| Blue Ridge School | Lynchburg Christian Academy | 4:00 p.m. | 42-6 | ||
| Fri. | September 29, 2000 | St. Christopher's School | Nansemond-Suffolk Academy | 4:00 p.m. | 7-18 |
| Colonial Beach High School | Christchurch School | 7:30 p.m. | 7-27 | ||
| Sat. | September 30, 2000 | George Mason | Quantico High School | 2:00 p.m. | |
| Virginia Episcopal School | St. Anne'-Belfield | 2:00 p.m. | 0-19 | ||
| Fri. | October 6, 2000 | Hampton Roads Academy | Greenbrier Christian Acad. | 7:00 p.m. | 7-34 |
| Potomac School | Maret School | 4:00 p.m. | |||
| Hampton Roads Academy | Greenbrier Christian Acad. | 7:00 p.m. | 7-34 | ||
| Hargrave Military Academy | Virginia Episcopal School | 3:30 p.m. | 34-7 | ||
| Lynchburg Christian Academy | Isle of Wight | 7:30 p.m. | 22-18 | ||
| Charlotte Latin | Massanutten Military Academy | 7:00 p.m. | 54-0 | ||
| Nansemond-Suffolk Academy | Benedictine High School | 7:30 p.m. | 22-17 | ||
| Sat. | October 7, 2000 | Quantico High School | Christchurch School | 1:30 p.m. | 27-28 |
| Fri. | October 13, 2000 | Hampton Roads Academy | St. Anne's-Belfield | 7:00 p.m. | 14-49 |
| Blue Ridge School | Christchurch School | 3:00 p.m. | 41-35 | ||
| Greenbrier Christian Academy | Broadwater Academy | 7:30 p.m. | 47-0 | ||
| Model School | Massanutten Military Academy | 7:00 p.m. | 22-50 | ||
| Sat. | October 14, 2000 | Potomac School | Sidwell Friends | 3:00 p.m. | 13-34 |
| Virginia Episcopal School | Bishop Ireton | 2:00 p.m. | |||
| Roanoke Catholic | Lynchburg Christian Acaemy | 7:30 p.m. | |||
| Norfolk Academy | Nansemond-Suffolk Academy | 2:00 p.m. | 45-33 | ||
| Fri. | October 20, 2000 | Nansemond-Suffolk Academy | Greenbrier Christian Academy | 7:30 p.m. | 21-0 |
| Lynchburg Christian Academy | North Cross | 7:30 p.m. | 12-21 | ||
| Sat. | October 21, 2000 | St. Christopher's School | St.Anne's-Belfield School | 3:00 p.m. | 21-16 |
| Catholic High School | Hampton Roads Academy | 1:30 p.m. | 41-0 | ||
| Blue Ridge School | Virginia Episcopal School | 2:00 p.m. | |||
| Massanutten Military Academy | Randolph-Macon Academy | 2:00 p.m. | 12-35 | ||
| Fri. | October 27, 2000 | Hampton Roads Academy | Blessed Sacrament-Huguenot | 7:00 p.m. | 21-28 |
| St. Anne's-Belfield | Blue Ridge School | 7:00 p.m. | 25-6 | ||
| Brunswick Acaemy | Potomac School | 7:00 p.m. | 0-51 | ||
| Greenbrier Christian Academy | Catholic High School | 7:30 p.m. | |||
| Fishburne Military Academy | Lynchburg Christian Academy | 3:30 p.m. | |||
| North Cross | Massanutten Military Academy | 3:00 p.m. | 32-14 | ||
| Sat. | October 28, 2000 | Virginia Episcopal School | Christchurch School | 2:00 p.m. | 18-27 |
| Randolph-Macon Academy | Nansemond-Suffolk Acaemy | 3:00 p.m. | 21-20 | ||
| Fri. | November 3, 2000 | St. Anne's-Belfield | Christchurch | 6:00 p.m. | 37-6 |
| Brunswick Academy | Quantico High School | 7:00 p.m. | |||
| Colonial Beach High School | Randolph-Macon Academy | 7:30 p.m. | 7-55 | ||
| Virginia Episcopal School | Hampton Roads Acaemy | 3:00 p.m. | 38-8 | ||
| Greenbrier Christian Academy | Lynchburg Christian Academy | 7:30 p.m. | 42-10 | ||
| Nansemond-Suffolk Academy | Collegiate School | 7:30 p.m. | 0-28 | ||
| Sat. | November 4, 2000 | Potomac School | Fairfield High School | 2:30 p.m. | |
| Fri. | November 10, 2000 | VISFA Playoffs | #3 St. Anne's-Belfield @ #2 Nansemond-Suffolk Acad. | ||
| November 11, 2000 | VISFA Playoffs | #4Greenbrier Christian @ #1Potomac School | |||
| Fri. | November 17, 2000 | VISFA Playoffs |