| Drew Wood record | ||||
|---|---|---|---|---|
| Year | School | Won | Lost | Title |
| 1999 | Homestead | 10 | 1 | |
| 2000 | Homestead | 10 | 2 | |
| 2001 | Homestead | 10 | 2 | |
| 2002 | Homestead | 10 | 1 | |
| 2003 | Homestead | 8 | 4 | |
| 2004 | Bloomington South | 7 | 4 | |
| 2005 | Bloomington South | 7 | 3 | |
| 2006 | Bloomington South | 9 | 3 | |
| 2007 | Bloomington South | 5 | 5 | |
| 2008 | Bloomington South | 8 | 3 | |
| 2009 | Bloomington South | 3 | 7 | |