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| Kent Chezem record |
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| Year | School | Won | Lost | Title | Class |
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| 1994-95 | Clinton Prairie | 5 | 16 | | 1A |
| 1995-96 | Clinton Prairie | 11 | 12 | | 4A |
| 1996-97 | Clinton Prairie | 12 | 9 | | 3A |
| 1997-98 | Clinton Prairie | 8 | 13 | | 1A |
| 1998-99 | Clinton Prairie | 10 | 12 | | 1A |
| 1999-00 | Clinton Prairie | 17 | 5 | | 4A |
| 2000-01 | Clinton Prairie | 12 | 9 | | 3A |
| 2001-02 | Clinton Prairie | 12 | 10 | | 3A |
| 2002-03 | Clinton Prairie | 14 | 9 | | 1A |
| 2003-04 | Clinton Prairie | 10 | 11 | | 3A |
| 2004-05 | Covington | 17 | 8 | sectional | 3A |
| 2005-06 | Covington | 11 | 11 | | 2A |
| 2006-07 | Covington | 13 | 10 | sectional | 1A |
| 2007-08 | Covington | 4 | 17 | | 1A |
| 2008-09 | Covington | 10 | 11 | | 4A |
| 2009-10 | Covington | 18 | 7 | sectional | 4A |
| 2010-11 | Covington | 16 | 6 | | 1A |
| 2011-12 | Covington | 9 | 12 | | 1A |
| 2012-13 | Covington | 14 | 8 | | 2A |
| 2013-14 | Covington | 18 | 2 | | 2A |
| 2014-15 | Covington | 22 | 2 | | 4A |
| 2015-16 | Loogootee | 14 | 11 | | 1A |
| 2016-17 | Loogootee | 21 | 8 | sectional | 4A |
| 2017-18 | Loogootee | 12 | 12 | | 2A |
| 2018-19 | Loogootee | 9 | 15 | | 1A |
| 2020-21 | North Judson | 8 | 14 | | 4A |
| 2021-22 | North Judson | 21 | 6 | sectional | 1A |
| 2022-23 | North Judson | 23 | 4 | sectional | 3A |
| 2023-24 | North Judson | 16 | 10 | regional | 1A |
| 2024-25 | North Judson | 9 | 14 | | 1A |
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