2024 Zoe Zuzak- 2023 Rachel Spencer
- 2022 Ryleigh Jackson
- 2021 Kate Wills
- 2020 Not Held
- 2019 Emily Yi
- 2018 Katie Allen
- 2017 Chloe Wildman
- 2016 Allison LaForce
- 2015 Jessica Bayuk
- 2014 Sarah Robinson
- 2013 Sabrina Frost
- 2012 Kennedy Taylor
- 2011 Ally Soule
- 2010 Mary Teal Mulligan
- 2009 Stephanie Meadowcroft
- 2008 Joanna Guy
- 2007 Kasey Staniszewski
- 2006 Hannah Mollerick
- 2005 Lindsay Morris
Prior to inception of the Outstanding Teen program the following young women held the title of Miss Teen Maryland: Brittany Eberly (04), Cynthia English (03), Tierra Wharton (02), Heather Molnar (01), Danielle McGarvey (00), Kelli Lobaugh (99), Amanda Daugherty (98)