Former Miss Delaware titleholders have gone on to lead accomplished lives. Many have entered into careers such as politics, law, education, entertainment, and medicine.{{fact|date=June 2014}}
The Miss Delaware Scholarship Organization provides several thousands of dollars in scholarships each year to its many contestants.
Joanna Wicks of Wilmington was crowned Miss Delaware on June 16, 2018. She competed for the title of Miss America 2019 on September 9, 2018 in Atlantic City, New Jersey.
The year in parentheses indicates the year of the Miss America competition the award/placement was garnered.
| Year | Name | Hometown | Age | Local Title | Miss America Talent | Placement at Miss America | Special scholarships at Miss America | Notes | | 2018 | Joanna Wicks[1] | Wilmington | 24 | Miss Wilmington | Speed Painting, "Confident" |
| 2017 | Chelsea Bruce[2] | Manasquan, NJ[3] | 21 | Miss Newark | Contemporary Dance | Eligible as a student at the University of Delaware[2] |
| 2016 | Amanda Debus[4][5] | Middletown | 23 | Miss First State | Contemporary Ballet | Previously Miss Delaware's Outstanding Teen 2008[5]
Previously Miss Delaware Teen USA 2011[6] |
| 2015 | Brooke Mitchell[7] | Selbyville | 19 | Miss Milford | Tap Dance/Baton Twirling, "Uptown Funk" | Non-finalist Talent Award | date=June 2018}} |
| 2014 | Brittany Lewis | Brigantine, NJ | 23 | Miss Wilmington | Jazz Dance | Quality of Life Award 1st runner-up | 1st runner-up at Miss Delaware 2014 pageant, assumed title when Longacre was dethroned[10] |
| Amanda Longacre | Bear | 24 | Miss Pike Creek | Vocal | N/A | Dethroned due to her not meeting the Miss America age requirement[8] |
| 2013 | Rebecca Jackson | Kennett Square, PA | 21 | Miss Dover | Vocal, "Think of Me" from The Phantom of the Opera | Non-finalist Talent Award |
| 2012 | Alyssa Murray | Selbyville | 20 | Miss Costal Bay | Jazz Dance, "River Deep – Mountain High" | Non-finalist Interview Award
Quality of Life Award Finalist |
| 2011 | Maria Cahill[9] | Newark | 20 | Miss Rehoboth Beach | Irish Dance, "Lord of the Dance" | Non-finalist Talent Award |
| 2010 | Kayla Martell | Milford | 21 | Miss Kent County | Contemporary Ballet en Pointe, "The Way You Make Me Feel" | Top 10 | Quality of Life Award 1st runner-up | date=June 2018}}
First contestant with alopecia areata to compete in Miss America pageant{{cn|date=June 2018}} |
| 2009 | Heather Lehman | Magnolia | 20 | Miss Diamond State | Classical Vocal, "Adele's Laughing Song" from Die Fledermaus |
| 2008 | Galen Giaccone[10] | Wyoming | 20 | Miss Diamond State | Piano, "El Cumbanchero" by Rafael Hernández Marín | Top 15 | Preliminary Talent Award |
| 2007 | Brittany Dempsey | Dover | 20 | Miss Capital | Jazz Dance, "Rhythm of the Night" |
| 2006 | Jamie Ginn | Wilmington | 25 | Miss Brandywine | Dance "Dancin' Fool" from Copacabana | date=June 2018}} |
| 2005 | Rebecca Bledsoe | Middletown | 23 | Miss Central Delaware | Classical Vocal "Una Voce Poco Fa" from The Barber of Seville | Non-finalist Talent Award |
| 2004 | Linda Kurtz | Dover | 21 | Miss Dover | Ballet "Man of La Mancha" | Quality of Life Award Finalist | date=June 2018}} |
| 2003 | Erin Elizabeth Williams | Lincoln | 20 | Miss Eastern Shore | Classical Vocal "Time to Say Goodbye" |
| 2002 | Shoha Parekh | Newark | 24 | Miss Greenville | Bharatnatyam Style Dance | Annapolis{{cn>date=June 2018}} |
| 2001 | Erin Cooper | Camden | 22 | Miss Hockessin | Lyrical Ballet, "Book of Days" |
| 2000 | Junnie Cross | Dover | 22 | Miss Hockessin | Vocal, "Wishing You Were Somehow Here Again" from The Phantom of the Opera | Bert Parks Talent Award
Bernie Wayne Scholarship for the Performing Arts Award
Preliminary Talent Award
Quality of Life Award Finalist |
| 1999 | Kama Boland | Hockessin | 22 | Miss Diamond State | Piano, "Jerry Lee Lewis Medley" |
| 1998 | Jody Kelly | Dover | 22 | Miss Hockessin | Flute, "Shenandoah" and "Dueling Banjos" |
| 1997 | Alison White | Millsboro | 18 | Miss Millsboro | Classical Vocal "Poor Wand'ring One" from The Pirates of Penzance | Non-finalist Talent Award |
| 1996 | Aimee Michelle Voshell | Felton | 18 | Miss Dover | Ballet en Pointe "Return to Innocence" |
| 1995 | Michelle Harris | Newark | 24 | Miss Brandywine | Vocal "I Will Always Love You" | Bert Parks Talent Award |
| 1994 | Letitia Lee Pusey | Millsboro | 23 | Miss Sussex County | Lyrical Tap Dance |
| 1993 | Jennifer Lin Kaczmarczyk | Hockessin | 20 | Miss Brandywine | Popular Vocal "This is the Moment" | Non-finalist Talent Award |
| 1992 | Kathleen Ann Slavin | Dagsboro | 25 | Miss Sussex County | Vocal "My Man" |
| 1991 | Beth Ann Jones | Wilmington | 22 | Miss Brandywine | Vocal Medley |
| 1990 | Lisa Marie Munzert | New Castle | 20 | Miss Brandywine | Dance / Twirling, "They're Playing Our Song" | Non-finalist Talent Award |
| 1989 | Robin Lee Coutant | Millsboro | 21 | Miss University | Vocal "Think of Me" |
| 1988 | Laura Kathleen Ludwig | Lewes | 21 | Miss Sussex County | Popular Vocal "Happy Days Are Here Again" |
| 1987 | Anne Marie Jarka | Newark | 21 | Miss University | Vocal / Piano, "Almost Over You" | George Cavalier Talent Award |
| 1986 | Lori Ann Scott | Wilmington | 23 | Miss Wilmington | Popular Vocal, "Love Is Spreading All Over" |
| 1985 | Lisa Anne Patrick | Newark | 24 | Miss Newark | Character Ballet en Pointe |
| 1984 | Nancy Lynn Ball | Rehoboth Beach | 24 | Miss Cape Henlopen | Jazz Ballet en Pointe |
| 1983 | Tammy Renee Copeland | Newark | 21 | Miss Greater Wilmington | Vocal "Cry Me a River" |
| 1982 | Nancy Ellen Farley | Elsmere | 21 | Miss New Castle | Comedy Monologue "Report of the Nominating Committee" |
| 1981 | Jodi Meade Graham | Wilmington | 19 | Miss Brandywine College | Vocal "Can You Read My Mind" | date=June 2018}} |
| 1980 | Andra Lee Dickerson | Newark | 21 | Miss Newark | Piano / Vocal |
| 1979 | Ann Lorraine Harrington | Milford | 22 | Miss Milford | Magic Act |
| 1978 | Janice Anne Albro | Claymont | 25 | Miss Brandywine Hundred | Piano Solo "The Entertainer" & "Maple Leaf Rag" | Preliminary Swimsuit Award |
| 1977 | Sandra Louise Aiken | Seaford | 21 | Miss Seaford | Classical Vocal "Quando me'n vo'" | Non-finalist Talent Award |
| 1976 | Debora Rica Lipford | Newark | 21 | Miss Newark | Dramatic Interpretation, "It Was a Good Time" from Ryan's Daughter | Top 10 | date=June 2018}} |
| 1975 | Elaine Campanelli | Ocean View | 20 | Miss Ocean View | Fire Baton Routine | Non-finalist Talent Award |
| 1974 | Kathleen Attanasi | Rehoboth Beach | 22 | Miss Rehoboth Beach | Harp Medley "Harmonious Blacksmith" & "Close To You" |
| 1973 | Jackie LaGuardia | Milford | 19 | Miss Sussex West | Vocal "Irma La Douce" |
| 1972 | Catherine Lawton[11] | Clayton | 20 | Miss University Motors | Banjo, "Banjo Memories" | Top 10 | Preliminary Talent Award |
| 1971 | Paula Kusmer | Wilmington | 19 | Miss Goldey-Beacom College | Dramatic reading from "The Diary of Anne Frank" | Miss Congeniality |
| 1970 | Linda Sue Hitchens | Seaford | 20 | Miss Nylon Capital | Vocal / Dance "Give My Regards to Broadway" |
| 1969 | Margo Ewing | Wilmington | 19 | Miss Talleyville | Vocal Interpretation "My Mother's Wedding Day" | date=June 2018}} |
| 1968 | Gayle Freeman | Wilmington | 19 | Miss Brandywine College | Vocal & Guitar "Times They Are a-Changin'" |
| 1967 | Susan Alice Levens | Dover | 18 | Miss Wesley College | Vocal, "Who Will Buy" from Oliver! |
| 1966 | Mary Lee Mancini | Wilmington | 19 | Miss Greater Wilmington | Ballet / Sketch (dance/monologue) |
| 1965 | Kathleen Grandall | Wilmington | 18 | Miss Brandywine | Multi-lingual Monologue with native songs & dances |
| 1964 | Anita Gail Euban | Wilmington | 20 | Miss Brandywine | Popular Vocal & Dance |
| 1963 | Diane Beverly Isaacs | Greenwood | Miss Greenwood | Piano & Popular Vocal | Was married to current United States Senator, Tom Carper[12] |
| 1962 | Alice Jane Watts | Lewes | 19 | Miss Harrington | Pantomime of Record "Seventeen" |
| 1961 | Robin Jane Whemper | Wilmington | 18 | Miss Newark | Vocal & Dance "That's What Makes Paris Paree" from April in Paris | Non-finalist Talent Award |
| 1960 | Deborah Dunkenfield Benoit | Wilmington | 21 | Composite Expression of Special Training |
| 1959 | Ester Olney | Newark | 18 | Vocal |
| 1958 | Nancy M. Williams | Wilmington | Dance "Gone With the Wind" |
| 1957 | Kathleen Ann D'Attillio | Wilmington | Piano |
| 1956 | Janice Olson | Newark |
| 1955 | Joanne Sakowski | Wilmington | Vocal |
| 1954 | Barbara Woodall | Claymont | Piano |
| 1953 | Lois Anne Alava | Wilmington | Piano "Concerto in A Minor" | Top 10 | Preliminary Talent Award |
| 1952 | Helen Blackwell | Wilmington | Classical Vocal |
| 1951 | Suzanne Parrott | Dover | Piano |
| 1950 | Lorna Edwardson | Dover | Classical Vocal "Un Bel Di" from Madame Butterfly |
| 1949 | No Delaware representative at Miss America pageant |
| 1948 |
| 1947 |
| 1946 |
| 1945 |
| 1944 | Jacquelyn Vasseur | Wilmington |
| 1943 | Mona Crawford | Wilmington |
| 1942 | Dorothy McGovern | Wilmington |
| 1941 | Verona Smith[13] | Bridgeville |
| 1940 | Peggy Insolo | Wilmington | Piano | Top 15 |
| 1939 | No Delaware representative at Miss America pageant |
| 1938 |
| 1937 | Nickey Harriet | Harrington |
| 1936 | Lillian Shamers | Wilmington |
| 1935 | No Delaware representative at Miss America pageant |
| 1934 | No pageant was held |
| 1933 | Victoria A. George | Wilmington | 18 |
| 1932 | No pageants were held |
| 1931 |
| 1930 |
| 1929 |
| 1928 |
| 1927 | No Delaware representative at Miss America pageant |
| 1926 |
| 1925 |
| 1924 |
| 1923 | Ruth Agnes Brady | Miss Wilmington | {{small|No Miss Delaware
Competed under local title at Miss America pageant}} |
| 1922 | Adele Senft | Miss Wilmington |
| 1921 | No Delaware representative at Miss America pageant |
1. ^{{cite web|first=Shleby |last=Vaccaro |title=Miss Wilmington gets promotion to Miss Delaware on a platform of domestic violence awareness |work=WDEL News |url=https://www.wdel.com/features/video-miss-wilmington-gets-promotion-to-miss-delaware-on-a/article_7547a0e8-71ea-11e8-ac5b-9b889ec5f469.html |date= June 17, 2018}}
2. ^1 {{cite web| title=Miss Newark named Miss Delaware 2017|publisher=Delaware State News|url=http://delawarestatenews.net/news/miss-newark-named-miss-delaware-2017/|date=June 16, 2017}}
3. ^{{cite web| title=Miss Delaware pageant to be held June 16 at Cape High in Lewes|publisher=Cape Gazette |url=http://www.capegazette.com/article/miss-delaware-pageant-be-held-june-16-cape-high-lewes/135183|date=June 12, 2017}}
4. ^{{cite web| title=Amanda Debus Is Miss Delaware 2016 |publisher=Delaware Today|url=http://www.delawaretoday.com/Amanda-Debus-Is-Miss-Delaware-2016/ |date=}}
5. ^1 {{cite web| first = Matt |last = Bittle |title=Middletown’s Debus ‘in such disbelief’ after Miss Delaware win |publisher=Delaware State News|url=https://delawarestatenews.net/entertainment/middletowns-debus-disbelief-miss-delaware-win/ |date=June 12, 2016}}
6. ^{{cite web |title=Amanda Debus Visits Section 36! |publisher=Section 36 |url=http://section-36.blogspot.com/2017/03/amanda-debus-visits-section-36.html|date=March 16, 2017}}
7. ^{{cite news |first=Arshon |last=Howard |newspaper=Delaware State News |publisher=Independent Newsmedia |location=Dover, DE |title=Brooke Mitchell crowned Miss Delaware 2015 |url=http://delawarestatenews.net/news/brooke-mitchell-crowned-as-miss-delaware-2015/ |date=June 13, 2015 |accessdate=June 14, 2015}}
8. ^1 {{cite web|url=http://abcnews.go.com/Entertainment/dethroned-miss-delaware-files-million-lawsuit/story?id=24602055|title=Dethroned Miss Delaware Amanda Longacre Files $3 Million Lawsuit|accessdate=|last=|first=|date=2014-07-17|publisher=ABC News}}
9. ^{{cite news|title=Maria Cahill crowned Miss Delaware|url=http://www.beaumontenterprise.com/news/article/Maria-Cahill-crowned-Miss-Delaware-1420950.php|publisher=Beaumont Enterprise|date=June 12, 2011}}{{dead link|date=February 2018 |bot=InternetArchiveBot |fix-attempted=yes }}
10. ^{{cite news|title=U of D student crowned Miss Delaware|publisher=WDel|url=http://www.wdel.com/story.php?id=739549075775|last=Associated Press|access-date=2008-06-17|archive-url=https://web.archive.org/web/20110720235914/http://www.wdel.com/story.php?id=739549075775|archive-date=2011-07-20|dead-url=yes|df=}}
11. ^{{cite news|title=Beauty Strums Way to Crown|url=https://www.newspapers.com/image/163569388/?terms=Catherine+Lawton|publisher=The News Journal|date=June 26, 1972}}
12. ^{{Cite news|url=https://thehill.com/blogs/blog-briefing-room/news/365035-dem-senator-denies-report-claiming-he-lied-about-abusing-his |title=Dem senator denies report claiming he lied about abusing his wife |last=Bowden |first=John |date=December 14, 2017 |work=The Hill| }}
13. ^{{cite news |title= Miss Delaware to Give Atlantic City Beauties Run for U. S. Honors |url=https://www.newspapers.com/newspage/160417518/ |publisher=The Morning News|location=Wilmington, Delaware |date=September 4, 1941}}
{{State pageantry|State=Delaware}}{{Miss America state}}