Henlopen Conference

• Milford won the first softball championship in 1976.

  Total Girls State Championships

Overall state championships

Notable sports alumni

• Walter "Huck" Betts of Millsboro was a pitcher for the Philadelphia Phillies and Boston Braves in the 1920s and 1930s, in the pre-draft years.
• Caleb "Tex" Warrington of Dover played center and guard for the Brooklyn Dodgers football team of the All-America Football Conference from 1946 to 1948 out of Auburn University.
• Carl Elliott of Laurel played defensive end and wide receiver for the Green Bay Packers from 1951 to 1954 out of the University of Virginia.
• Forest "Spook" Jacobs of Milford was a second baseman for the Philadelphia Athletics, Kansas City Athletics, and Pittsburgh Pirates from 1954–1956, is one of only two players in Major League Baseball history to go 4 for 4 in his first major league game, and is a 1991 inductee to the Delaware Sports Museum and Hall of Fame.
• Chris Short of Milford was a pitcher for the Philadelphia Phillies and Milwaukee Brewers from 1959 to 1973, beginning in the pre-draft years.
• Carl Ergenzinger of Dover was drafted as a catcher and third baseman in the ninth round for the Houston Astros in 1965, the first year of the formal Major League Baseball Draft.
• Danny LeBright of Milford was a pitcher for the Houston Astros, making the team in a 1967 tryout.
• Thomas Sullivan of Dover was drafted as a pitcher in the eleventh round by the Cleveland Indians in 1969.
• Randy Lee of Laurel was drafted as a pitcher in the 15th round by the Baltimore Orioles in 1970.
• Renie Martin of Dover was drafted as pitcher in the 9th round by the San Francisco Giants in 1976 out of the University of Richmond.
• Ralph Jean of Dover was a pitcher drafted by the Oakland Athletics in the 33rd round of the 1978 draft.
• Randy Bush of Dover was drafted as an outfielder by the Minnesota Twins in the 2nd round in 1979 out of the University of New Orleans.
• Robert Nichols of Delmar was drafted as a pitcher by the Pittsburgh Pirates in the 14th round of the 1980 draft.
• Julie Dayton of Laurel was first team All-American in lacrosse in 1980 and 1981 out of Longwood College, was a ten-year member of Team USA from 1980 to 1990, was the head field hockey coach for University of Virginia and Dartmouth College, and is a 2003 inductee into the Delaware Sports Museum and Hall of Fame.
• Oliver Maull of Lewes was drafted as a catcher by the Baltimore Orioles in the 26th round of the 1981 draft.
• Mike Meade of Dover played fullback for the Green Bay Packers and Detroit Lions from 1982 to 1985 out of Pennsylvania State University.
• Bob Vantrease of Seaford was drafted as a pitcher by the Oakland Athletics in the 29th round of the 1983 draft out of the University of Delaware.
• Doug Willey of Bridgeville was drafted as a pitcher by the Atlanta Braves in the 15th round of the 1985 draft out of Essex Community College.
• Warren McGee of Seaford was signed by the Philadelphia Phillies as a pitcher after the 1986 draft.
• Delino DeShields of Seaford was drafted as a second baseman by the Montreal Expos as the 12th overall pick in the 1st round in 1987 out of Villanova University and is one of only two players in Major League Baseball history to collect four hits in their major league debut, had career totals of 1548 hits, 872 runs scored, 561 RBIs, and 463 stolens bases. He was named the Baltimore Orioles Most Valuable Player in 2000 and is a 2006 inductee into the Delaware Sports Museum and Hall of Fame.
• Clarence Bailey of Milford played as a fullback for the Miami Dolphins in 1987 out of Hampton University.
• Pat Wright of Camden was drafted as a catcher by the Oakland Athletics in the 32nd round of the 1988 draft.
• Michael Neill of Seaford was drafted as an outfielder by the Oakland Athletics in the 2nd round of the 1991 draft out of Villanova University, won an Olympic Gold Medal with the United States Olympic Baseball team, won 5 state championships in Little League, advanced three times to the Little League World Series, 1991 Big East Player of the Year, and is a 2005 inductee to the Delaware Sports Museum and Hall of Fame.
• Stoney Briggs of Seaford was drafted as an outfielder by the Toronto Blue Jays in the 8th round of the 1991 draft out of Delaware Technical & Community College.
• Mark Harris of Camden was drafted as a shortstop by the Chicago White Sox in the 17th round of the 1991 draft.
• Ben Cephas of Seaford was drafted as an outfielder by the Milwaukee Brewers in the 27th round of the 1992 draft out of Delaware Technical & Community College.
• Frank Roberts of Seaford was drafted as a pitcher by the Florida Marlins in their inaugural draft in 1993 in the 72nd round.
• Brad Lee of Lewes was drafted as an outfielder by the Texas Rangers in the supplemental draft in 1994 out of Delaware Technical & Community College.
• Brian Miflin of Lewes was drafted as an outfielder by the New York Mets in the 50th round of the 1994 draft out of Delaware Technical & Community College.
• Mike Riley of Seaford was drafted as a pitcher by the San Francisco Giants in the 16th round of the 1996 draft out of West Virginia University.
• Lovett Purnell of Seaford was drafted as a tight end and wide receiver by the New England Patriots in the 7th round of the 1996 draft and played for the Baltimore Ravens as well, was drafted by the Chicago White Sox, was captain of the West Virginia University football team and named to the WVU All-Century Team, named All-Big East, and played in Super Bowl XXXI, and was a 2007 inductee into the Delaware Sports Museum Hall of Fame.
• Erik McLaughlin was signed by the Atlanta Braves after a try-out in 1996.
• Rob Meyers of Felton was signed by the Minnesota Twins after a try-out in 1997.
• Dave Williams of Camden was drafted as a pitcher by the Pittsburgh Pirates in 1998.
• Luke Petitgout of Georgetown was drafted as an offensive lineman by the New York Giants as the 19th overall pick of the 1999 draft out of the University of Notre Dame.
• Ian Snell of Dover was drafted as a pitcher by the Pittsburgh Pirates in the 26th round in the 2000 draft.
• Mark Comoli of Millsboro was drafted as a pitcher by the Toronto Blue Jays in the 25th round of the 2001 draft out of Delaware Technical & Community College.
• Isiah Wright of Dover was drafted as a pitcher by the Montreal Expos in the 15th round of the 2002 draft.
• Shawn Phillips of Laurel was drafted as a pitcher by Texas Rangers in the 2004 draft out of Delaware State University.
• Derrick Gibson of Seaford was drafted as a shortstop and pitcher by the Boston Red Sox in the 2nd round of the 2008 draft.
• Theodis Bowe of Ellendale was drafted as a center fielder by the Cincinnati Reds in the 21st round of the 2008 draft.
• Jerell Allen of Milford was drafted as a center fielder by the Kansas City Royals in the 11th round of the 2011 MLB draft.
• Devon Reed of Milford was drafted as a shortstop by the Florida Marlins in the 20th round of the 2011 MLB draft.
• Nicholas Grant of Milford was drafted as a pitcher by the New York Mets in the 15th round of the 2012 MLB draft.
• Professional wrestlers Jamin and Mark Pugh, The Briscoe Brothers, of Laurel received honorable mention all-state for football in both their junior and senior years of high school.
• Carrie Lingo of Rehoboth Beach played field hockey for University of North Carolina Tar Heels where she was a two-time All-ACC honoree, won a National Championship in 1997, was a national runner-up in 2000, and was named to the ACC 50th Anniversary Team as one of the top field hockey players in conference history. After college, she represented the United States in the Pan American Cup, Pan American Games, World Cup, Olympic qualifier and the Beijing Olympics. She was elected to the Delaware Sports Hall of Fame in 2015.