Miss Maine Softball Winners
| Year | Position | Name | School |
| 1999 | P | Jesse Becher | Oxford Hills |
| 2000 | P | Dee Regan | Portland |
| 2001 | C | MeghanYoung | Portland |
| 2002 | 2B | Megan Ramos | Noble |
| 2003 | C | Kat Vincent | St Dom’s |
| 2004 | P | Sam St.Hilaire | Leavitt |
| 2005 | C | Brittany Morin | Winslow |
| 2006 | P | Monica White | Cony |
| 2007 | P | Kelsey Griffin | Scarborough |
| 2008 | P | Amy Hackett | Bangor |
| 2009 | P | Hannah Hill | Fryeburg |
| 2010 | P | Sam Bedore | Bangor |
| 2011 | P | Alexis Bogdanovich | South Portland |
| 2012 | P | Julia Geaumont | Thornton Academy |
| 2013 | SS | Danica Gleason | South Portland |
| 2014 | P | Alyssa Williamson | Scarborough |
| 2015 | P | Bailey Tremblay | Thornton Academy |
| 2016 | P | Karli Theberge | Hermon |
| 2017 | C | Hailey Perry | Hermon |
| 2018 | P/OF | Chloe Griffin | Scarborough |
| 2019 | P | Olivia Howe | Thornton Academy |
| 2020 | Bella Dickinson | Scarborough |
Bella Dickinson named Miss Maine Softball 2020