The schools and teams that make up the Henlopen Conference are divided into two divisions, the Henlopen Northern Division and Henlopen Southern Division. Despite the name, the schools are not divided by geographical location, but rather by enrollment numbers, with the larger schools in the Northern Division and the smaller schools in the Southern Division. The conferences are re-arranged every few years based on enrollment numbers.
The current conference alignment for the schools along with the city they are located in are:
The Henlopen Conference was created in the January 1959 as a conference of Sussex County schools with enrollments under 350. The conference began its first interleague conference play with the start of the 1959 high school baseball season. The initial members of the Henlopen Conference were the Bridgeville Mustangs, Rehoboth Beach Seahawks, Milton Warriors, Greenwood Foresters, Delmar Wildcats, Millsboro Blue Devils, John M. Clayton Bears, Lord Baltimore Lords, and Selbyville Rebels. While an initial member of the newly formed conference, the Delmar Wildcats did not join the conference for interleague conference play until the beginning of the 1959–60 basketball season. Two weeks later, on February 3, 1959, the Harrington Lions and Felton Green Devils were admitted, expanding the league into Kent County. The Dover Air Force Base Falcons joined two years after its formation.
In 1969, additional teams were added as the Diamond State Conference, originally formed by the larger schools of Kent and Sussex County, merged with the Henlopen Conference. These were: Smyrna, Dover, Caesar Rodney, Milford, Seaford, Lewes, Georgetown and Middletown; Middletown being the lone member from New Castle County. Lewes and Georgetown were the first schools that decided to migrate from the Diamond State Conference and join and eventually every team from the Diamond State Conference (except for Middletown) joined the Henlopen Conference. Middletown, as the only New Castle County school, moved to a conference composed entirely of New Castle County schools after one year of playing as an independent because they were barred from joining the Henlopen Conference due to the conference by-laws regarding geography.
Because of the state mandated school district mergers of 1969–70, the teams changed their geographical makeup. Lewes, Milton, and Rehoboth Beach merged to form the Cape Henlopen Vikings. Georgetown, John M. Clayton, and a large part of the Millsboro School District merged to become the Sussex Central Golden Knights (the other portion of Millsboro was absorbed into Cape Henlopen). Greenwood and Bridgeville merged to become the Woodbridge Blue Raiders. Harrington and Felton merged with Frederica to become the Lake Forest Spartans. Lord Baltimore and Selbyville were merged with Frankford and Dagsboro to become the Indian River Indians. The Milford School District also joined the conference after merging with the Ellendale and Houston school districts, keeping the Milford Buccaneers name. Magnolia and Oak Point merged with Caesar Rodney in 1969 and Dover Air Force Base high school students were absorbed into the Caesar Rodney High School after the United States government closed down the base's school in the 1980s. The Polytech Panthers (1992) and Sussex Tech Ravens (1995) joined the conference with the addition of their sports teams when the schools made the transition from vocational trade schools to technical and academic schools. In August 2015, the Sussex Academy of Arts and Sciences became the newest school, and first charter school, to join the Henlopen Conference.[1]
Of note is that not all teams joined the conference immediately at its inception, affecting the number of conference championships the teams could have won.
Since 1969, teams in the Henlopen Conference have won a total of 25 state football championships. The south leads the north in championships 16 to 9. Caesar Rodney leads the northern division with three Division I Championships and Delmar leads the southern division with six Division II Championships. Woodbridge High School was the last team to win a state championship in 2016.
Only three times has the conference swept the Division I and Division II championship. In 1988, Dover from the North and Indian River from the South were the first to do it. In 2008, Caesar Rodney (North) and Milford (South) accomplished the feat. In the 2008 championship games, both Caesar Rodney and Milford defeated Sussex Central and Laurel to win their respective championships, marking the only time the final four teams in the state tournament were from the Henlopen Conference.[2] In the latest occasion, Woodbridge won the Division II championship and Smyrna won the Division I championship in 2016.
Seaford High School is the only school in the conference to win both a Division I and II Championship.
In 2006 Lake Forest High School had to temporarily shut down their varsity football team due to allegations of use of painkillers. Lake Forest forfeited their final eight games for that season.[3][4]
Prior to the 2007–08 school year, Milford was moved to the Henlopen South while Smyrna joined the Northern Division due to changes in enrollment. On September 30, 2008, those numbers were rechecked and confirmed to determine the assignments for the 2009–10 and 2010-11 school years. With only a total of 8 students separating the seventh and eighth largest schools, with Polytech coming in a 1,164 and Milford at 1,156; the conference assignments were certified to stay the same through June 2011. This included Polytech in the North Division and Milford in the South.[5]
Days prior to the Division 2 Championship game, Polytech High School challenged the enrollment numbers that were submitted by Milford High School. Polytech brought their case to the athletic directors of the Henlopen Conference schools in a monthly meeting, and Milford argued their case as to why the numbers were correct. At the center of Polytech's argument were 17 students of the Intensive Learning Center, a separate school from Milford High School for special needs and mentally challenged students that rented space inside Milford High. The Polytech officials argued that those students were in the building and should be counted, the Milford officials argued that it was a separate school and that the State of Delaware did not count those children in Milford's enrollment nor did Milford receive funding for them.
A vote was held by the athletic directors of the various schools in the conference, all of the directors in the South voted Milford should move up to the North except Laurel High School; all of the directors in the North said Milford should stay down except for Polytech High School, which made it a 6–6 vote as Milford was not allowed to vote. However, the director for Sussex Central wasn't present for the meeting, so the director for Indian River High School was allowed to vote twice as Indian River High School and Sussex Central High School are in the same school district. The director voted two times that Milford move to the North Division and the vote was confirmed.
In December 2008, Milford appealed to the superintendents of the schools comprising the Henlopen Conference. The superintendents voted to uphold the decision of the athletic directors as it was an athletics issue. Milford also appealed to the Delaware Interscholastic Athletic Association, the governing body for athletics in Delaware schools. The DIAA decided that the matter needed to be handled by the Henlopen Conference and that they would not be involved.
On April 15, 2009, Milford High School filed a lawsuit against the Henlopen Conference in Chancery Court challenging that the vote was against the conference by-laws. In the lawsuit, Milford is listed as seeking "declaratory relief" and to have the vote to change the conference alignments nullified, placing Milford High School back in the South Division.[6][7] On July 2, that lawsuit was dismissed.[8]
Delaware high school playoffs were expanded from a four team field in both Division I and Division II to six team field for both divisions beginning with the 2004 season.
Of note: Teams with a gold background went on to win the State Championship.
Year
Henlopen South (Div II)
Henlopen North (Div I)
2020
Woodbridge
Smyrna
2019
Delmar
Smyrna
2018
Woodbridge
Sussex Central
2017
Delmar
Smyrna
2016
Woodbridge
Smyrna
2015
Lake Forest
Smyrna
2014
Lake Forest
Sussex Tech
2013
Indian River
Caesar Rodney
2012
Indian River
Sussex Central
2011
Indian River
Sussex Central
2010
Lake Forest
Sussex Central
2009
Delmar
Sussex Tech
2008
Milford
Sussex Central
2007
Delmar
Sussex Central
2006
Delmar
Sussex Central
2005
Indian River
Dover
2004
Indian River
Caesar Rodney
2003
Indian River
Caesar Rodney
2002
Delmar
Sussex Central
2001
Delmar
Dover
2000
Delmar
Caesar Rodney
1999
Woodbridge
Caesar Rodney
1998
Delmar
Cape Henlopen
1997
Delmar
Cape Henlopen
1996
Delmar
Caesar Rodney
1995
Delmar
Caesar Rodney
1994
Seaford
Caesar Rodney
1993
Laurel
Seaford
1992
Laurel
Seaford
1991
Lake Forest
Caesar Rodney
1990
Lake Forest
Caesar Rodney
1989
Lake Forest
Caesar Rodney
1988
Indian River
Dover
1987
Indian River
Seaford
1986
Laurel, Indian River, Smyrna
Seaford, Caesar Rodney, Dover
1985
Delmar
Seaford
1984
Lake Forest
Cape Henlopen
1983
Seaford
Caesar Rodney
1982
Seaford
Dover, Cape Henlopen
1981
Lake Forest
Seaford
1980
Indian River
Caesar Rodney
1979
Indian River
Cape Henlopen
1978
Dover Air Force Base***
Caesar Rodney
1977
Smyrna
Caesar Rodney
1976
Delmar
Caesar Rodney
1975
Smyrna
Caesar Rodney
1974
Smyrna
Milford
1973
Smyrna
Caesar Rodney, Sussex Central
1972
Lake Forest
Dover
1971
Laurel
Dover
1970
Indian River
Sussex Central
1969
Indian River
Smyrna
(*** Dover Air Force High School shut down operations and merged with Caesar Rodney High School. The two schools have always been in the same school district.)
Prior to 1969 there were no North and South divisions, simply an overall champion. They were:
Year
Henlopen Conference Champion
1968
Indian River
1967
Bridgeville (Woodbridge)
1966
Bridgeville (Woodbridge)
1965
Delmar
1964
Harrington (Lake Forest)
1963
John M. Clayton (Indian River)
1962
Millsboro / John M. Clayton (Sussex Central / Indian River)
1961
Rehoboth (Cape Henlopen)
1960
Millsboro / Rehoboth (Sussex Central / Cape Henlopen)
1959
Bridgeville (Woodbridge)
Note that of those pre-1969 teams listed above, only Indian River and Delmar still exist as school districts today, with Indian River's merger coming prior to the 1969–70 school year.
Battle of the Bell Milford vs. Lake Forest – Started in 1969 when the conferences were formed and school districts were consolidated. The winning team keeps the trophy, the bell off a train that used to run between Milford and Harrington, for a year until the next Battle of the Bell.
2013 Battle of the Bell Champion – Lake Forest (33-7)
Delaware's Oldest High School Rivalry Seaford vs. Laurel – The oldest rivalry game in the state, and said to be the third oldest rivalry in the nation, these two towns are separated by only 61⁄2 miles and a large turn-out is always expected.
2013 Delaware's Oldest High School Rivalry Champion – Laurel (46-6)
The Civil War Caesar Rodney vs. Dover – A cross-town rivalry game in Dover.
2013 Civil War Champion – Caesar Rodney (42-18)
The Battle for Georgetown Sussex Tech vs. Sussex Central – A cross-town rivalry game in Georgetown.
2013 Battle for Georgetown Champion – Sussex Tech (28-27)
The Tech Bowl Sussex Tech vs. Polytech – A rivalry game between Sussex County and Kent County's two technical high schools.
2013 Tech Bowl Champion – Sussex Tech (35-28)
The Harvest Bowl Smyrna vs. Middletown – A non-conference rivalry game going back to before the Henlopen Conference when the two teams played in the Diamond State Conference.
2012 Harvest Bowl Champion – Middletown (47-19)
Did not play in 2013
Battle for the Lions Club Trophy Delmar vs. Laurel – The two towns are only 9 miles apart along U.S. 13 and the winner takes home a trophy sponsored by the local Lions Club.
2013 Battle for the Lions Club Trophy Champion – Delmar (21-20)
Intra-district Rivalry Sussex Central vs. Indian River – A rivalry game between the two schools that belong to the Indian River School District. The IRSD is one of the largest districts in the state of Delaware.
2013 Intra-district Rivalry Champion – Sussex Central (29-27)
Prior to 1969 there were no conferences, simply a Tournament champion. In 1970 the school districts consolidated. Of those pre-1969 teams, only Indian River and Delmar still exist as school districts today, with Indian River's merger coming prior to 1969–70.
Total Division Championships:
Caesar Rodney – 21 (most all time in the North)
Cape Henlopen – 1
Delmar – 0
Dover – 7
Indian River – 2
Lake Forest – 0
Laurel – 2
Milford – 6 *Only team to win championships in both the North & South (2 in North, 4 in South)
Polytech – 0
Seaford – 0
Smyrna – 29 (Most by any school, in any conference, in any sport in the state)
Sussex Central – 7
Sussex Tech – 0
Woodbridge – 0
Conference Dual Meet Championships (Overall Champion):
Caesar Rodney – 16 (most all time)
Cape Henlopen – 0
Delmar – 0
Dover – 4
Indian River – 0
Lake Forest – 0
Laurel – 0
Milford – 2 *One of only 2 Sussex County schools to win overall championship
Polytech – 0
Seaford – 0
Smyrna – 12
Sussex Central – 5 *One of only 2 Sussex County schools to win overall championship
Sussex Tech – 0
Woodbridge – 0
Tournament championships:
Caesar Rodney – 10 (most all time)
Cape Henlopen – 0
Delmar – 2
Dover – 7
Indian River – 0
Lake Forest – 2 *Both won by Harrington prior to 1970 merger
Laurel – 0
Milford – 0
Polytech – 0
Seaford – 0
Smyrna – 4
Sussex Central – 4
Sussex Tech – 0
Woodbridge – 0
Prior to 1970 the conference was broken down into East and West based on geographic location. An Eastern Division and Western Division Champion was declared and a championship game was played between the two to determine the Henlopen Conference Champion. No division champions were declared in 1960 and 1961, instead the team with the best record was named Henlopen Conference Champion.
Year
Henlopen West Division
Henlopen East Division
Conference Championship Game
Conference Champion
1969
Dover Air Force Base
Rehoboth
Dover Air Force Base 77 – Rehoboth 70
Dover Air Force Base
1968
Bridgeville
Milton
Bridgeville 65 – Milton 58
Bridgeville
1967
Bridgeville
Milton
Milton 54 – Bridgeville 52
Milton
1966
Felton
Milton
Milton 60 – Felton 58
Milton
1965
Felton
Milton
Felton 73 – Milton 58
Felton
1964
Felton
Lord Baltimore
Felton 81 – Lord Baltimore 59
Felton
1963
Felton
Rehoboth
Rehoboth 48 – Felton 44
Rehoboth
1962
Greenwood
Milton
Milton 46 – Greenwood 38
Milton
1961
No Division Champion
No Division Champion
No Game
Rehoboth
1960
No Division Champion
No Division Champion
No Game
Rehoboth
Note that of those pre-1969 teams listed above, none still exist as an independent school district.
Total division championships:
Caesar Rodney – 3 *Includes 1 won by Dover Air Force Base
Cape Henlopen – 21 *Includes 2 won by Rehoboth (does not included 1960 & 1961) and 5 won by Milton (Most in the North Division and all time)
Delmar – 0
Dover – 4
Indian River – 19 *Includes 1 won by Lord Baltimore (Most in the South Division)
Lake Forest – 10 *Includes 2 won by Felton
Laurel – 0
Milford – 3
Polytech – 2
Seaford – 4 (3 in North, 1 in South)
Smyrna – 6 (3 in North, 3 in South)
Sussex Central – 3
Sussex Tech – 3
Woodbridge – 7 *Includes 2 won by Bridgeville and 1 won by Greenwood
Total Henlopen Conference Championships:
Caesar Rodney – 3 *Includes 1 won by Dover Air Force Base
Cape Henlopen – 15 *Includes 3 won by Rehoboth and 3 won by Milton
Delmar – 0
Dover – 4
Indian River – 6
Lake Forest – 4 *Includes 2 won by Felton
Laurel – 0
Milford – 2
Polytech – 0
Seaford – 3
Smyrna – 3
Sussex Central – 1
Sussex Tech – 3
Woodbridge – 2 *Includes 1 won by Bridgeville
The following Henlopen Conference boys teams have gone on to win state championships (includes pre-merger teams). Of note, if (I/II) appears in the division category, all divisions play for the only state championship.[28]
The Unified Division was added in 2016 and is a DIAA recognized athletic division partnering students with and without disabilities in conjunction with Special Olympics Delaware.[29]
The Middletown Cavaliers won the first outdoor track championship in 1942 as a member of the Diamond State Conference, a precursor to the Henlopen Conference which Middletown is not a part of as they are in New Castle County.
1977 was the only year for a Division 1 & 2 North and Division 1 & 2 South for outdoor track.
The Unified Division was added in 2015 and is a DIAA recognized athletic division partnering students with and without disabilities in conjunction with Special Olympics Delaware.[30]
The following Henlopen Conference girl teams have gone on to win state championships (includes pre-merger teams). Of note, if (I/II) appears in the division category, all divisions play for the only state championship. There were no girls championships until the 1973–1974 school year, all championships are post-merger.[28]
Cape Henlopen's win for lacrosse in 2009 was the first time a public high school had won the girls lacrosse state championship ever in Delaware, which started in 1998.[31]
Chris Short of Milford (Milford Buccaneers) was a pitcher for the Philadelphia Phillies and Milwaukee Brewers from 1959 to 1973, beginning in the pre-draft years.
Robert Nichols of Delmar (Delmar Wildcats) was drafted as a pitcher by the Pittsburgh Pirates in the 14th round of the 1980 draft.
Julie Dayton of Laurel (Laurel Bulldogs) 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 (Cape Henlopen Vikings) was drafted as a catcher by the Baltimore Orioles in the 26th round of the 1981 draft.
Bob Vantrease of Seaford (Seaford Blue Jays) 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 (Woodbridge Blue Raiders) 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 (Seaford Blue Jays) was signed by the Philadelphia Phillies as a pitcher after the 1986 draft.
Delino DeShields of Seaford (Seaford Blue Jays) 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 (the other was Milford's Spook Jacobs), had career totals of 1548 hits, 872 runs scored, 561 RBIs, and 463 stolen 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 (Milford Buccaneers) played as a fullback for the Miami Dolphins in 1987 out of Hampton University.
Pat Wright of Camden (Caesar Rodney Riders) was drafted as a catcher by the Oakland Athletics in the 32nd round of the 1988 draft.
Michael Neill of Seaford (Seaford Blue Jays) 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.
Mark Harris of Camden (Caesar Rodney Riders) was drafted as a shortstop by the Chicago White Sox in the 17th round of the 1991 draft.
Ben Cephas of Seaford (Seaford Blue Jays) 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 (Seaford Blue Jays) was drafted as a pitcher by the Florida Marlins in their inaugural draft in 1993 in the 72nd round (the draft was extended for the expansion teams).
Brad Lee of Lewes (Cape Henlopen Vikings) 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 (Cape Henlopen Vikings) 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 (Seaford Blue Jays) 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 (Seaford Blue Jays) 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.[33]
Erik McLaughlin (Polytech Panthers) was signed by the Atlanta Braves after a try-out in 1996.
Rob Meyers of Felton (Lake Forest Spartans) was signed by the Minnesota Twins after a try-out in 1997.
Dave Williams of Camden (Caesar Rodney Riders) was drafted as a pitcher by the Pittsburgh Pirates in 1998.
Ian Snell (aka Ian Oquendo) of Dover (Caesar Rodney Riders) was drafted as a pitcher by the Pittsburgh Pirates in the 26th round in the 2000 draft.
Mark Comoli of Millsboro (Indian River Indians) 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 (Dover Senators) was drafted as a pitcher by the Montreal Expos in the 15th round of the 2002 draft.
Shawn Phillips of Laurel (Laurel Bulldogs) was drafted as a pitcher by Texas Rangers in the 2004 draft out of Delaware State University.
Derrick Gibson of Seaford (Seaford Blue Jays) was drafted as a shortstop and pitcher by the Boston Red Sox in the 2nd round of the 2008 draft.
Jerell Allen of Milford (Milford Buccaneers) was drafted as a center fielder by the Kansas City Royals in the 11th round of the 2011 MLB draft.[34]
Devon Reed of Milford (Milford Buccaneers) was drafted as a shortstop by the Florida Marlins in the 20th round of the 2011 MLB draft.
Nicholas Grant of Milford (Milford Buccaneers) was drafted as a pitcher by the New York Mets in the 15th round of the 2012 MLB draft.[35]
Professional wrestlers Jamin and Mark Pugh, The Briscoe Brothers, of Laurel (Laurel Bulldogs) received honorable mention all-state for football in both their junior and senior years of high school.
Zack Gelof of Rehoboth Beach (Cape Henlopen Vikings) played baseball for the University of Virginia Cavaliers when he was drafted as a second baseman by Oakland Athletics in the 2nd round of the 2021 MLB draft.
^Brian Citino, "Senators earn top honors in Henlopen" Dover Post, March 2, 2010, found at Dover PostArchived 2011-07-18 at the Wayback Machine. Accessed March 4, 2010.