Chess - Champions
| Champions | |
|---|---|
| YEAR | SCHOOL |
| 2023-24 | Mason |
| 2022-23 | Mason |
| 2021-22 | Mason |
| 2020-21 | Mason |
| 2019-20 | Mason |
| 2018-19 | Mason |
| 2017-18 | Mason |
| 2016-17 | Mason |
| 2015-16 | Sycamore |
| 2014-15 | Mason |
| 2013-14 | Mason |
| 2012-13 | Mason |
| 2011-12 | Mason |
| 2010-11 | Sycamore |
| 2009-10 | Sycamore |
| 2008-09 | Sycamore |
| 2007-08 | Sycamore |
| 2006-07 | Sycamore |
| 2005-06 | Lakota West, Sycamore |
| 2004-05 | Sycamore |
| 2003-04 | Lakota East |
| 2002-03 | Princeton |
| 2001-02 | Princeton, Sycamore |
| 2000-01 | Middletown |
| 1999-2000 | Lakota West |
| 1998-99 | Sycamore |
| 1997-98 | Sycamore |
| 1996-97 | Sycamore |
| 1995-96 | Sycamore |
| 1994-95 | Sycamore |
| 1993-94 | Sycamore |
| 1992-93 | Sycamore |
| 1991-92 | Sycamore |
| 1990-91 | Princeton |
| 1989-90 | Fairfield |
| 1988-89 | Princeton |
| 1987-88 | Fairfield, Lakota |
| 1986-87 | Fairfield |
| 1984-85 | Princeton |
| 1983-84 | Princeton |
| 1982-83 | Lakota |
| 1981-82 | Fairfield |
| 1980-81 | Princeton |
| 1979-80 | Princeton |
| 1978-79 | Princeton |
| 1977-78 | Fairfield, Hamilton Taft |
| 1976-77 | Princeton |
| 1975-76 | Middletown |
