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======  Crestwood All-Time Football Results ======

^ Year      ^ Record       ^ Coach          ^ Extra Info ^
| 1973 | 2-8 | Paul Wolf |  |
| 1974 | 2-6-1 | Paul Wolf |  |
| 1975 | 7-1-1 | Paul Wolf |  |
| 1976 | 6-4 | Paul Wolf |  |
| 1977 | 9-0-1 | Paul Wolf |  |
| 1978 | 7-3 | Paul Wolf |  |
| 1979 | 5-5 | Paul Wolf |  |
| 1980 | 4-6 | Paul Wolf |  |
| 1981 | 4-6 | Paul Wolf |  |
| 1982 | 2-7-1 | Marty Taush |  |
| 1983 | 3-6-1 | Marty Taush |  |
| 1984 | 7-3 | Don Faix |  |
| 1985 | 1-9 | Don Faix |  |
| 1986 | 4-6 | Jerry Berton |  |
| 1987 | 9-1 | Jerry Berton |  |
| 1988 | 5-5 | Jerry Berton |  |
| 1989 | 7-3 | Jerry Berton |  |
| 1990 | 10-0 | Jerry Berton |  |
| 1991 | 2-8 | Jerry Berton |  |
| 1992 | 5-5 | Jerry Berton |  |
| 1993 | 3-7 | Jerry Berton |  |
| 1994 | 2-8 | Tom Hannan |  |
| 1995 | 5-5 | Tom Hannan |  |
| 1996 | 7-3 | Tom Hannan |  |
| 1997 | 9-2 | Tom Hannan | won conference championship game  |
| 1998 | 9-2 | Tom Hannan | lost conferece championship game |
| 1999 | 8-3 | Tom Hannan | Playoffs |
| 2000 | 7-3 | Tom Hannan |  |
| 2001 | 8-3 | Tom Hannan | Playoffs |
| 2002 | 6-4 | Tom Hannan |  |
| 2003 | 3-7 | Tom Hannan |  |
| 2004 | 8-2 | Tom Hannan |  |
| 2005 | 6-4 | Tom Hannan |  |
| 2006 | 6-4 | Tom Hannan |  |
| 2007 | 4-6 | Tom Hannan |  |
| 2008 | 3-7 | Tom Hannan |  |
| 2009 | 2-8 | Tom Hannan |  |
| 2010 | 5-5 | Chris Kosiorek  |  |
| 2011 | 2-8 | Chris Kosiorek  |  |
| 2012 | 4-6 | Pete Thompson |  |
| 2013 | 5-5 | Pete Thompson |  |
| 2014 | 9-2 | Pete Thompson | Playoffs |
| 2015 | 10-3 | Pete Thompson | Regional Runner-up |
| 2016 | 9-2 | Pete Thompson | Playoffs |
| 2017 | 1-7 | Nate Peters | 2 games inexplicably canceled |
| 2018 | 5-5 | Nate Peters |  |
| 2019 | 6-4 | Nate Peters |  |
| 2020 | 3-6 | Jack D’Amato | Playoffs |
| 2021 | 7-4 | Jack D’Amato | League Champions/2nd Round Playoffs |
| 2022 | 4-6 | Jack D’Amato |  |
| 2023 | 5-6 | Jack D’Amato | Playoffs  |

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