- 2024 Bridget O’Brien – Frederick, Maryland
- 2023 Kennedy Taylor – Silver Spring
- 2022 Kayla Willing – Marion
- 2021 Lydia Sohn – Bethesda
- 2020 Allison Redman -Bel Air
- 2019 Caitlyn Stupi – Westminster
- 2018 Adrianna David – Rockville
- 2017 Kathleen Masek (Heinle) – Westminster
- 2016 Hannah Brewer (Curtwright) – Manchester
- 2015 Destiny Clark – Gaithersburg
- 2014 Jade Kenny—Madison
- 2013 Christina Denny (McDaniel) – Owings Mills
- 2012 Joanna Guy – Swanton
- 2011 Carlie Colella (Mazzei)- Hagerstown
- 2010 Lindsay Staniszewski – Edgewater
- 2009 Brooke Poklemba – Westminster
- 2008 Louise Schlegel (Wood)- Silver Spring
- 2007 Shana Powell (Oshiro) – Bowie
- 2006 Brittany Lietz (Cicala) – Edgewater
- 2005 Rachel Ellsworth (Jacovino) – Fort Ashby, WV
- 2004 Tiffany Jenkins (Leatherberry) – Silver Spring
- 2003 Marina Harrison (Cooper) – Severna Park
- 2002 Camille Lewis (France)- Rockville
- 2001 Kelly Glorioso (Fodel) – Hydes
- 2000 Sonia Maria Amir (Bowie) – Beltsville
- 1999 Keri L. Schrader (Barta) – Rockville
- 1998 Heather Noelle Davis (Epkins) – Severna Park
- 1997 Jaime Fox (Hardwick) – Frederick
- 1996 Susan Alexander (Thompson) – Silver Spring
- 1995 Marcia M. Griffith (Davis)-Fort Washington
- 1994 Karissa Brooke Jones (Horowicz) – Hagerstown
- 1993 1993 Renee Cole – Bowie
- 1992 Tammy Wyatt (Roberts) – Clinton
- 1991 Debra Renea Fries (Baker) – Waldorf
- 1990 Kimberly Ann Grimm (Weimer) – Mt. Lake Park
- 1989 Virginia Cha – Frederick
- 1988 Lori Ann Windsor (Hunt) – Mt. Airy
- 1997 Tamara Alaine Walker(Panzarella)-Kingsville
- 1986 Katrina Lynn Owens – Pikesville
- 1985 Jennifer Louise Charlton (Shuldes)-Bethesda
- 1984 Mary Elizabeth Haroth, D.D.S. (Neill) – Towson
- 1983 Amy Elizabeth Keys – Lanham
- 1982 Lynne Carol Graham (Postel) – Bethesda
- 1981 Robin Valeria Harmon – Hagerstown
- 1980 Lisa Marie Daskal (Voohries) – Cumberland
- 1979 Shelly Meg Peiken – Greenbelt
- 1978 Caroline JoAnn Donnelly – College Park
- 1977 Donna Maria Silvestri (Davis) – Catonsville
- 1976 Barbara Jean Jennings (Mathews) – Greenbelt
- 1975 Veronica Marie Clark – Bel Air
- 1974 Susan Jane Wohlfarth (Sainato)- Potomac
- 1973 Kristi Maurine Reindl (Vetri) – La Vale
- 1972 Kathleen (Kathy) Louise Neff – Cumberland
- 1971 Joan Michele Ehrgott (Chirieleison)-Avondale
- 1970 Sharon Anne Cannon (Dashiell) – Salisbury
- 1969 Margaret Elaine Mackle (Bowman)-Cecilton
- 1968 Karen Anne Hansen (Schulze) – College Park
- 1967 Ingrid Christine Larson – Ellicot City
- 1966 Linda Rita Peluzzo (Townsend) – Oxon Hill
- 1965 Barbara Lynn Hamilton – College Park
- 1964 Dona Marie McCauley (Magee) – Rockville
- 1964 **Sharon Rae Burlingham – Aberdeen
- 1963 Carolyn Bond Wright (Jones)- Forrest Hill
- 1962 Beverly Ann Smith (Thiel) – Esses
- 1961 Patricia Ann Moon (Fresh Smith) – Bethesda
- 1960 Robin Carole Davis (Dodson) – Hyattsville
- 1959 Marie Lorraine True (Evans) – Phoenix
- 1958 *Mary Roberta Page (Baxter) – Bethesda
- 1957 Nancy Elizabeth Norris (Lacy) – Silver Spring
- 1956 Jeanette Louise Rosensteel – Timonium
- 1955 Carol Jennette (Shook) – Westminster
- 1954 Phyllis Yvonne Leftwich (Schmidt) – Dundalk
- 1953 Meta Frances Justice (Davis) – Crisfield
- 1952 *Shirley Virginia Harrison -Baltimore
- 1951 Georgia Reed (Baker) – Baltimore
- 1950 Annamae “Ann” Urie (Kipp) – Baltimore
- 1949 Jean Crow (Kiser) – Baltimore
- 1948 *Juanita Lookabaugh (McIntyre)-Cumberland
- 1947 Carolyn Jean Dixon (Mertens) – Cumberland
- 1946 Dorothy C. Crockett (Eckels) – Baltimore
- 1945 Virginia Lee Van Sant (Manning)- Cumberland
- 1944 Audrey Klingenberg (Koeniger)- Baltimore
- 1943 Lillian Marlene Huber – Baltimore
- 1942 Bettye Mitchell – Baltimore
- 1941 *Helen Claire Pender (D’Anrea)
- 1940 Marie Beiser – Baltimore
- 1939 Elaine Pasqualla (Sturgeon) – Crisfield
- 1938 *Yolanda Emily Ugarte (McMartin)-Baltimore
- 1937 May Vivian Miller – Baltimore
- 1936 Ethel Mae Holland (Bunting) – Berlin
*Deceased **Sharon Rae Burlington, Aberdeen, formerly Miss Harford County, assumed the duties of Miss Maryland, when Miss McCauley resigned in January 1965.