| CHARLESTOWN PIRATES Won 34, Lost 42 | |||||||
|---|---|---|---|---|---|---|---|
| YEAR | ROUND | OPPONENT | SCORE | ||||
| 1984 | Sectional | Lawrenceburg | L | 6 | 33 | ||
| 1985 | Sectional | Brown County | L | 21 | 30 | ||
| 1986 | Sectional | at | Greensburg | L | 14 | 35 | |
| 1987 | Sectional | Mitchell | W | 45 | 6 | ||
| Sectional | at | Washington | W | 36 | 6 | ||
| Sectional | at | Evansville Memorial | L | 0 | 21 | ||
| 1988 | Sectional | Evansville Memorial | L | 12 | 46 | ||
| 1989 | Sectional | North Harrison | W | 39 | 0 | ||
| Sectional | at | Princeton | W | 30 | 21 | ||
| Sectional | Evansville Memorial | W | 32 | 22 | |||
| Regional | at | Greensburg | W | 37 | 0 | ||
| Semistate | Indianapolis Roncalli | L | 0 | 14 | |||
| 1990 | Sectional | North Harrison | W | 28 | 13 | ||
| Sectional | at | Jasper | L | 6 | 14 | ||
| 1991 | Sectional | at | Brownstown Central | W | 42 | 14 | |
| Sectional | at | Salem | W | 10 | 0 | ||
| Sectional | Lawrenceburg | L | 26 | 27 | 2OT | ||
| 1992 | Sectional | Brown County | W | 29 | 23 | 2OT | |
| Sectional | at | Greensburg | L | 6 | 27 | ||
| 1993 | Sectional | Mitchell | W | 42 | 14 | ||
| Sectional | at | Greensburg | W | 56 | 41 | ||
| Sectional | Salem | W | 35 | 7 | |||
| Regional | at | Evansville Memorial | L | 0 | 24 | ||
| 1994 | Sectional | Salem | L | 8 | 21 | ||
| 1995 | Sectional | at | Salem | L | 7 | 28 | |
| 1996 | Sectional | Tell City | W | 36 | 28 | OT | |
| Sectional | North Harrison | W | 65 | 20 | |||
| Sectional | at | Edgewood | W | 32 | 16 | ||
| Regional | Heritage Hills | L | 14 | 62 | |||
| 1997 | Sectional | Lawrenceburg | L | 14 | 35 | ||
| 1998 | Sectional | at | Clarksville | W | 36 | 28 | |
| Sectional | Lawrenceburg | L | 14 | 47 | |||
| 1999 | Sectional | at | Lawrenceburg | L | 19 | 44 | |
| 2000 | Sectional | at | Providence | L | 0 | 16 | |
| 2001 | Sectional | at | Indian Creek | L | 28 | 48 | |
| 2002 | Sectional | at | Brownstown Central | L | 22 | 48 | |
| 2003 | Sectional | Brownstown Central | L | 0 | 35 | ||
| 2004 | Sectional | Brownstown Central | L | 9 | 41 | ||
| 2005 | Sectional | Clarksville | L | 7 | 33 | ||
| 2006 | Sectional | at | Providence | L | 8 | 31 | |
| 2007 | Sectional | at | Brown County | W | 49 | 20 | |
| Sectional | Heritage Hills | L | 24 | 42 | |||
| 2008 | Sectional | North Harrison | W | 33 | 15 | ||
| Sectional | at | Heritage Hills | L | 6 | 32 | ||
| 2009 | Sectional | Indian Creek | L | 0 | 20 | ||
| 2010 | Sectional | Edgewood | W | 28 | 21 | ||
| Sectional | Brown County | W | 54 | 20 | |||
| Sectional | at | Indian Creek | L | 28 | 48 | ||
| 2011 | Sectional | North Harrison | W | 56 | 0 | ||
| Sectional | Corydon Central | L | 28 | 33 | |||
| 2012 | Sectional | Mitchell | W | 82 | 0 | ||
| Sectional | Corydon Central | W | 49 | 6 | |||
| Sectional | at | Brownstown Central | W | 62 | 10 | ||
| Regional | Gibson Southern | L | 49 | 57 | |||
| 2013 | Sectional | Corydon Central | W | 28 | 7 | ||
| Sectional | at | Brown County | W | 41 | 24 | ||
| Sectional | at | Brownstown Central | L | 6 | 62 | ||
| 2014 | Sectional | Corydon Central | W | 15 | 6 | ||
| Sectional | Brownstown Central | W | 27 | 16 | |||
| Sectional | at | North Harrison | W | 18 | 7 | ||
| Regional | Heritage Hills | L | 7 | 28 | |||
| 2015 | Sectional | Heritage Hills | W | 39 | 37 | ||
| Sectional | Brownstown Central | L | 19 | 44 | |||
| 2016 | Sectional | North Harrison | L | 14 | 17 | ||
| 2017 | Sectional | at | Batesville | L | 22 | 38 | |
| 2018 | Sectional | at | Salem | L | 20 | 27 | |
| 2019 | Sectional | Brownstown Central | W | 7 | 6 | ||
| Sectional | at | Lawrenceburg | L | 18 | 49 | ||
| 2020 | Sectional | Greensburg | L | 0 | 36 | ||
| 2021 | Sectional | Greensburg | L | 21 | 24 | ||
| 2022 | Sectional | at | Salem | W | 35 | 12 | |
| Sectional | Heritage Hills | L | 25 | 35 | |||
| 2023 | Sectional | at | Heritage Hills | L | 14 | 51 | |
| 2024 | Sectional | at | Martinsville | L | 0 | 56 | |
| 2025 | Sectional | Silver Creek | W | 51 | 26 | ||
| Sectional | at | Martinsville | L | 20 | 52 | ||
| SECTIONAL CHAMPIONSHIPS | ||
|---|---|---|
| YEAR | CLASS | DATE |
| 1989 | 3A | Nov. 3, 1989 |
| 1993 | 3A | Nov. 5, 1993 |
| 1996 | 3A | Nov. 1, 1996 |
| 2012 | 3A | Nov. 2, 2012 |
| 2014 | 3A | Nov. 7, 2014 |
| REGIONAL CHAMPIONSHIPS | ||
| 1989 | 3A | Nov. 10, 1989 |