Prior District 1 Softball Champions
| Year | | Little League Softball | 8-10 Year Old | 9-11 Year Old | Juniors | Seniors |
| 2024 | | Wilton | Wilton
| New Canaan ***
| | |
| 2023 | | Wilton | New Canaan
| | | |
| 2022 | |
| Darien | Wilton |
|
|
| 2021 | | Darien | Wilton |
|
|
|
| 2020 | | Wilton |
|
|
|
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| 2019 | | Wilton | Darien | Wilton |
|
|
| 2018 | | Darien | New Canaan |
|
|
|
| 2017 | | Darien | Darien | Wilton | New Canaan |
|
| 2016 | | Rowayton | Darien |
| New Canaan |
|
| 2015 | | New Canaan | Darien | Darien/Rowayton |
|
|
| 2014 | | Redding-Easton | Redding-Easton |
|
|
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| 2013 | | Darien | Redding-Easton |
|
|
|
| 2012 | | Darien | Redding-Easton | Darien | Greenwich | Greenwich |
| 2011 | | Darien | Redding-Easton |
| Greenwich | Greenwich |
| 2010 | | Darien | Darien |
| Greenwich | Greenwich |
| 2009 | | Darien | Darien |
| Ridgefield |
|
| 2008 | | Redding-Easton | Darien | Redding-Easton | Ridgefield |
|
| 2007 | | Redding-Easton | Darien | Ridgefield | Ridgefield |
|
| 2006 | | Ridgefield |
|
|
|
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| 2005 | | Darien | Darien |
|
|
|
| 2004 | | Darien | Darien |
|
|
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| 2003 | | Darien | Darien |
|
|
|
| 2002 | | Darien | Darien |
| Darien |
|
| 2001 | | Darien |
|
| Darien |
|
| 2000 | | Darien |
|
| Darien |
|
| 1999 | | Darien |
|
| Wilton |
|
| 1998 | | Wilton |
|
| Wilton |
|
| 1997 | | Wilton |
|
| Wilton |
|
| 1996 | | Wilton |
|
| Wilton |
|
| 1995 | | Wilton |
|
|
|
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| 1994 | | Stamford Northrop |
|
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| 1993 | | Stamford Northrop |
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+++ Sectional Champions
*** State Champions