| Date | Time | Away | | Home | | |
|---|
| Sat, Sep 12, 2009 | 1:30 pm | John Marshall | 13 | Jamestown | 14 | * |
| final in overtime; at James City County Stadium |
| Fri, Sep 18, 2009 | 7:30 pm | Grafton | 21 | Jamestown | 16 | |
| FINAL |
| Sat, Sep 26, 2009 | 7:30 pm | Jamestown | 34 | York | 35 | |
| final in overtime; at Bailey Field |
| Sat, Oct 3, 2009 | 7:30 pm | Poquoson | 21 | Jamestown | 7 | |
| final; at James City County Stadium |
| Fri, Oct 9, 2009 | 7:30 pm | Jamestown | 34 | Warhill | 6 | |
| Final |
| Fri, Oct 16, 2009 | 7:00 pm | Bruton | 0 | Jamestown | 9 | |
| Final |
| Fri, Oct 23, 2009 | 7:30 pm | Jamestown | 6 | Tabb | 30 | |
| final |
| Fri, Oct 30, 2009 | 7:30 pm | New Kent | 13 | Jamestown | 35 | |
| final; at Cooley Field |
| Fri, Nov 6, 2009 | 7:30 pm | Jamestown | 20 | Smithfield | 14 | |
| Final |
| Sat, Nov 14, 2009 | 7:30 pm | Lafayette | 7 | Jamestown | 31 | |
| James City County Stadium (ppd from Friday) |