| Date | H/A | W/L | Team | Score | Opponent | Score | |
| 2008-08-29 | H | W | Calvin Coolidge (DC) | 36 | Gonzaga (DC) (0) | 34 | 1659 |
| 2008-09-05 | H | W | Calvin Coolidge (DC) | 20 | Friendship Collegiate (DC) (3) | 18 | 1676 |
| 2008-09-12 | H | W | Calvin Coolidge (DC) | 53 | McKinley (DC) (3) | 0 | 1661 |
| 2008-09-19 | A | L | Calvin Coolidge (DC) | 25 | Bridgeport (6) | 46 | 679 |
| 2008-10-03 | A | W | Calvin Coolidge (DC) | 57 | Anacostia (DC) (1) | 0 | 1994 |
| 2008-10-10 | A | W | Calvin Coolidge (DC) | 50 | Roosevelt(DC) (1) | 10 | 1663 |
| 2008-10-17 | H | W | Calvin Coolidge (DC) | 40 | Wilson (DC) (0) | 14 | 2006 |
| 2008-10-24 | A | W | Calvin Coolidge (DC) | 47 | Hyde Leadership (DC) (0) | 8 | 1665 |
| 2008-10-31 | A | L | Calvin Coolidge (DC) | 27 | Dunbar (DC) (0) | 34 | 1666 |
| 2008-11-07 | A | Calvin Coolidge (DC) | Cardozo (DC) (1) | 1667 |