# Henlopen Conference

The Henlopen Conference is a high school sports conference comprising public schools in Kent County and Sussex County in lower Delaware. The teams participate in a variety of sports including football, boys and girls soccer, track and field, cross country, boys and girls basketball, boys and girls indoor track, boys and girls outdoor track, wrestling, boys and girls lacrosse, baseball, softball, cheerleading, boys and girls swimming, and field hockey.

## Schools and teams

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:
Henlopen Northern Division
| School | Team | City | Geographic areas served |
| Caesar Rodney | Riders | Camden | Camden, Wyoming, Dover Air Force Base, Magnolia, Woodside |
| Cape Henlopen | Vikings | Lewes | Lewes, Rehoboth Beach, Milton, Harbeson, Cedar Creek, Broadkill Beach |
| Dover | Senators | Dover | Dover, Cheswold, Hartly, Little Creek, Leipsic |
| Polytech | Panthers | Woodside | Kent County technical students |
| Smyrna | Eagles | Smyrna | Smyrna, Clayton, Kenton |
| Sussex Central | Golden Knights | Georgetown | Georgetown, Millsboro |
| Sussex Tech | Ravens | Georgetown | Sussex County technical students |
| Milford | Buccaneers | Milford | Milford, Ellendale, Houston, Lincoln, Thompsonville, Slaughter Beach |
Henlopen Southern Division
| School | Team | City | Geographic areas |
| Delmar | Wildcats | Delmar | Delmar |
| Indian River | Indians | Dagsboro | Dagsboro, Frankford, Bethany Beach, Millville, Ocean View, Gumboro, Angola, Oak Orchard, Selbyville, Fenwick Island |
| Lake Forest | Spartans | Felton | Felton, Bowers Beach, Frederica, Harrington, Viola |
| Laurel | Bulldogs | Laurel | Laurel, Bethel |
| Seaford | Blue Jays | Seaford | Seaford, Blades |
| Sussex Academy of Arts and Sciences | Seahawks | Georgetown | Sussex County - Charter school with lottery-selected admission |
| Woodbridge | Blue Raiders | Bridgeville | Bridgeville, Greenwood, Farmington |

### Membership timeline

Full members Full members (non-football) Assoc. members (football only) Assoc. member (list sports)

## Conference history

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.
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.

## Football
### Football history

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. 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.

### 2006 Lake Forest forfeits

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.

### Milford controversy

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.
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. On July 2, that lawsuit was dismissed.

### Historical Henlopen Conference football records
#### 1950s
##### 1959 Regular season Football Standings

Henlopen Conference
| School | Team | Conference record | Overall record | Season Outcome |
| Bridgeville | Mustangs | 6 - 0 | 6 - 3 | No playoffs |
| Rehoboth Beach | Seahawks | 5 - 1 | 5 - 4 | No playoffs |
| Millsboro | Blue Devils | 4 - 2 | 6 - 2 | No playoffs |
| Harrington | Lions | 2 - 3 - 1 | 3 - 4 - 1 | No playoffs |
| Lord Baltimore | Lords | 2 - 4 | 3 - 6 | No playoffs |
| John M. Clayton | Bears | 1 - 4 - 1 | 2 - 5 - 1 | No playoffs |
| Selbyville | Rebels | 0 - 6 | 0 - 6 | No playoffs |

#### 1960s
##### 1960 Regular season Football Standings

Henlopen Conference
| School | Team | Conference record | Season Outcome |
| Millsboro | Blue Devils | 6 - 1 | No playoffs |
| Rehoboth Beach | Seahawks | 6 - 1 | No playoffs |
| Delmar | Wildcats | 5 - 2 | No playoffs |
| Bridgeville | Mustangs | 4 - 3 | No playoffs |
| John M. Clayton | Bears | 4 - 3 | No playoffs |
| Harrington | Lions | 1 - 6 | No playoffs |
| Lord Baltimore | Lords | 1 - 6 | No playoffs |
| Selbyville | Rebels | 1 - 6 | No playoffs |

##### 1961 Regular season Football Standings

Henlopen Conference
| School | Team | Conference record | Season Outcome |
| Rehoboth Beach | Seahawks | 7 - 0 | No playoffs |
| John M. Clayton | Bears | 6 - 1 | No playoffs |
| Millsboro | Blue Devils | 5 - 2 | No playoffs |
| Bridgeville | Mustangs | 4 - 3 | No playoffs |
| Delmar | Wildcats | 3 - 4 | No playoffs |
| Harrington | Lions | 1 - 5 - 1 | No playoffs |
| Selbyville | Rebels | 1 - 5 - 1 | No playoffs |
| Lord Baltimore | Lords | 0 - 7 | No playoffs |

##### 1962 Regular season Football Standings

Henlopen Conference
| School | Team | Conference record | Season Outcome |
| Millsboro | Blue Devils | 6 - 0 - 1 | No playoffs |
| John M. Clayton | Bears | 5 - 0 - 2 | No playoffs |
| Bridgeville | Mustangs | 4 - 3 | No playoffs |
| Delmar | Wildcats | 4 - 3 | No playoffs |
| Rehoboth Beach | Seahawks | 3 - 3 - 1 | No playoffs |
| Lord Baltimore | Lords | 3 - 4 | No playoffs |
| Harrington | Lions | 0 - 6 - 1 | No playoffs |
| Selbyville | Rebels | 0 - 6 - 1 | No playoffs |

##### 1963 Regular season Football Standings

Henlopen Conference
| School | Team | Conference record | Overall record | Season Outcome |
| John M. Clayton | Bears | 7 - 0 | 8 - 0 | No playoffs |
| Millsboro | Blue Devils | 6 - 1 | 7 - 2 | No playoffs |
| Bridgeville | Mustangs | 3 - 2 - 2 | 5 - 2 - 2 | No playoffs |
| Rehoboth Beach | Seahawks | 3 - 3 - 1 | 3 - 3 - 1 | No playoffs |
| Harrington | Lions | 3 - 4 | 3 - 5 | No playoffs |
| Lord Baltimore | Lords | 2 - 4 - 1 | 3 - 4 - 1 | No playoffs |
| Delmar | Wildcats | 1 - 6 | 1 - 8 | No playoffs |
| Selbyville | Rebels | 1 - 6 | 3 - 6 | No playoffs |

##### 1964 Regular season Football Standings

Henlopen Conference
| School | Team | Conference record | Overall record | Season Outcome |
| Harrington | Lions | 8 - 0 - 1 | 8 - 0 - 1 | No playoffs |
| Bridgeville | Mustangs | 7 - 1 - 1 | 7 - 1 - 1 | No playoffs |
| Millsboro | Blue Devils | 5 - 2 - 1 | 5 - 2 - 1 | No playoffs |
| Dover Air Force | Falcons | 5 - 4 | 5 - 4 | No playoffs |
| John M. Clayton | Bears | 3 - 3 - 3 | 3 - 3 - 3 | No playoffs |
| Rehoboth Beach | Seahawks | 3 - 3 - 3 | 3 - 3 - 3 | No playoffs |
| Delmar | Wildcats | 4 - 4 | 4 - 4 | No playoffs |
| Selbyville | Rebels | 1 - 6 - 1 | 1 - 6 - 1 | No playoffs |
| Milton | Warriors | 1 - 5 | 1 - 5 | No playoffs |
| Lord Baltimore | Lords | 0 - 9 | 0 - 9 | No playoffs |

##### 1965 Regular season Football Standings

Henlopen Conference
| School | Team | Conference record | Overall record | Season Outcome |
| Delmar | Wildcats | 8 - 1 | 8 - 1 | No playoffs |
| John M. Clayton | Bears | 7 - 1 - 1 | 7 - 1 - 1 | No playoffs |
| Dover Air Force | Falcons | 6 - 3 | 6 - 3 | No playoffs |
| Lord Baltimore | Lords | 5 - 4 | 5 - 4 | No playoffs |
| Rehoboth Beach | Seahawks | 5 - 4 | 5 - 4 | No playoffs |
| Harrington | Lions | 4 - 5 | 4 - 5 | No playoffs |
| Millsboro | Blue Devils | 4 - 5 | 4 - 5 | No playoffs |
| Bridgeville | Mustangs | 3 - 5 - 1 | 3 - 5 - 1 | No playoffs |
| Milton | Warriors | 2 - 7 | 2 - 7 | No playoffs |
| Selbyville | Rebels | 0 - 9 | 0 - 9 | No playoffs |

#### 2000s
##### 2002 Regular season Football Standings

Henlopen Northern Division
| School | Team | Division Record | Overall record | Season Outcome |
| Sussex Central | Golden Knights | 5 - 0 | 9 - 2 | Loss in semifinals of Div. I playoffs |
| Caesar Rodney | Riders | 4 - 1 | 6 - 4 | Failed to make playoffs |
| Dover | Senators | 3 - 2 | 5 - 5 | Failed to make playoffs |
| Sussex Tech | Ravens | 2 - 3 | 4 - 6 | Failed to make playoffs |
| Cape Henlopen | Vikings | 1 - 4 | 2 - 8 | Failed to make playoffs |
| Seaford | Blue Jays | 0 - 5 | 2 - 8 | Failed to make playoffs |
Henlopen Southern Division
| School | Team | Division Record | Overall record | Season Outcome |
| Delmar | Wildcats | 6 - 0 | 10 - 0 | Won Div. II State Championship |
| Laurel | Bulldogs | 5 - 1 | 9 - 2 | Loss in semifinals of Div. II playoffs |
| Smyrna | Eagles | 4 - 2 | 8 - 2 | Failed to make playoffs |
| Milford | Buccaneers | 2 - 4 | 5 - 5 | Failed to make playoffs |
| Indian River | Indians | 2 - 4 | 4 - 6 | Failed to make playoffs |
| Lake Forest | Spartans | 2 - 4 | 4 - 6 | Failed to make playoffs |
| Woodbridge | Blue Raiders | 0 - 6 | 2 - 8 | Failed to make playoffs |

##### 2003 Regular season Football Standings

Henlopen Northern Division
| School | Team | Division Record | Overall record | Season Outcome |
| Caesar Rodney | Riders | 5 - 0 | 9 - 2 | Loss in first round of Div. I playoffs |
| Sussex Central | Golden Knights | 4 - 1 | 8 - 2 | Failed to make playoffs |
| Dover | Senators | 3 - 2 | 5 - 5 | Failed to make playoffs |
| Sussex Tech | Ravens | 2 - 3 | 5 - 5 | Failed to make playoffs |
| Cape Henlopen | Vikings | 1 - 4 | 2 - 8 | Failed to make playoffs |
| Seaford | Blue Jays | 0 - 5 | 3 - 7 | Failed to make playoffs |
Henlopen Southern Division
| School | Team | Division Record | Overall record | Season Outcome |
| Smyrna | Eagles | 5 - 1 | 9 - 2 | Loss in semifinals of Div. II playoffs |
| Indian River | Indians | 5 - 1 | 7 - 4 | Loss in semifinals of Div. II playoffs |
| Lake Forest | Spartans | 4 - 2 | 6 - 4 | Failed to make playoffs |
| Milford | Buccaneers | 3 - 3 | 5 - 5 | Failed to make playoffs |
| Laurel | Bulldogs | 3 - 3 | 4 - 6 | Failed to make playoffs |
| Woodbridge | Blue Raiders | 1 - 5 | 2 - 7 | Failed to make playoffs |
| Delmar | Wildcats | 0 - 6 | 1 - 9 | Failed to make playoffs |

##### 2004 Regular season Football Standings

Henlopen Northern Division
| School | Team | Division Record | Overall record | Season Outcome |
| Caesar Rodney | Riders | 5 – 0 | 9 – 2 | Loss in semifinals of Div. I playoffs |
| Sussex Tech | Ravens | 4 – 1 | 7 – 4 | Loss in first round of Div. I playoffs |
| Milford | Buccaneers | 3 – 2 | 7 – 3 | Failed to make playoffs |
| Sussex Central | Golden Knights | 2 – 3 | 5 – 5 | Failed to make playoffs |
| Dover | Senators | 1 – 4 | 3 – 7 | Failed to make playoffs |
| Cape Henlopen | Vikings | 0 – 5 | 0 – 10 | Failed to make playoffs |
Henlopen Southern Division
| School | Team | Division Record | Overall record | Season Outcome |
| Indian River | Indians | 5 – 1 | 8 – 4 | Loss in semifinals of Div. II playoffs |
| Woodbridge | Blue Raiders | 4 – 2 | 7 – 3 | Failed to make playoffs |
| Smyrna | Eagles | 4 – 2 | 7 – 4 | Loss in first round of Div. II playoffs |
| Laurel | Bulldogs | 4 – 2 | 7 – 4 | Loss in first round of Div. II playoffs |
| Delmar | Wildcats | 2 – 4 | 3 – 7 | Failed to make playoffs |
| Seaford | Blue Jays | 1 – 5 | 3 – 7 | Failed to make playoffs |
| Lake Forest | Spartans | 1 – 5 | 3 – 7 | Failed to make playoffs |
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.

##### 2005 Regular season Football Standings

Henlopen Northern Division
| School | Team | Division Record | Overall record | Season Outcome |
| Dover | Senators | 5 – 0 | 8 – 3 | Loss in first round of Div. I playoffs |
| Caesar Rodney | Riders | 3 – 2 | 4 – 6 | Failed to make playoffs |
| Sussex Central | Golden Knights | 2 – 3 | 6 – 5 | Loss in first round of Div. I playoffs |
| Sussex Tech | Ravens | 2 – 3 | 5 – 5 | Failed to make playoffs |
| Cape Henlopen | Vikings | 2 – 3 | 4 – 6 | Failed to make playoffs |
| Milford | Buccaneers | 1 – 4 | 4 – 6 | Failed to make playoffs |
Henlopen Southern Division
| School | Team | Division Record | Overall record | Season Outcome |
| Indian River | Indians | 6 – 0 | 9 – 2 | Loss in semifinals of Div. II playoffs |
| Laurel | Bulldogs | 5 – 1 | 8 – 3 | Loss in first round of Div. II playoffs |
| Delmar | Wildcats | 4 – 2 | 8 – 2 | Failed to make playoffs |
| Lake Forest | Spartans | 3 – 3 | 4 – 6 | Failed to make playoffs |
| Smyrna | Eagles | 2 – 4 | 5 – 5 | Failed to make playoffs |
| Woodbridge | Blue Raiders | 1 – 5 | 3 – 7 | Failed to make playoffs |
| Seaford | Blue Jays | 0 – 6 | 0 – 10 | Failed to make playoffs |

##### 2006 Regular season Football Standings

Henlopen Northern Division
| School | Team | Division Record | Overall record | Season Outcome |
| Sussex Central | Golden Knights | 5 – 0 | 11 – 1 | Loss in Div. I Championship Game |
| Milford | Buccaneers | 3 – 2 | 6 – 4 | Failed to make playoffs |
| Cape Henlopen | Vikings | 3 – 2 | 5 – 5 | Failed to make playoffs |
| Caesar Rodney | Riders | 2 – 3 | 5 – 5 | Failed to make playoffs |
| Dover | Senators | 3 – 3 | 5 – 5 | Failed to make playoffs |
| Sussex Tech | Ravens | 0 – 5 | 2 – 8 | Failed to make playoffs |
Henlopen Southern Division
| School | Team | Division Record | Overall record | Season Outcome |
| Delmar | Wildcats | 6 – 0 | 11 – 1 | Loss in Div. II Championship Game |
| Indian River | Indians | 5 – 1 | 8 – 3 | Loss in first round of Div. II playoffs |
| Woodbridge | Blue Raiders | 4 – 2 | 6 – 4 | Failed to make playoffs |
| Laurel | Bulldogs | 3 – 3 | 6 – 4 | Failed to make playoffs |
| Smyrna | Eagles | 2 – 4 | 3 – 7 | Failed to make playoffs |
| Seaford | Blue Jays | 1 – 5 | 2 – 8 | Failed to make playoffs |
| Lake Forest | Spartans | 1 – 5 | 1 – 9 | Failed to make playoffs |

##### 2007 Regular season Football Standings

Henlopen Northern Division
| School | Team | Division Record | Overall record | Season Outcome |
| Sussex Central | Golden Knights | 6 – 0 | 10 – 2 | Loss in Div. I Championship Game |
| Caesar Rodney | Riders | 4 – 2 | 6 – 5 | Loss in first round of Div. I playoffs |
| Sussex Tech | Ravens | 4 – 2 | 7 – 3 | Failed to make playoffs |
| Dover | Senators | 3 – 3 | 5 – 5 | Failed to make playoffs |
| Cape Henlopen | Vikings | 3 – 3 | 4 – 6 | Failed to make playoffs |
| Smyrna | Eagles | 1 – 5 | 3 – 7 | Failed to make playoffs |
| Polytech | Panthers | 0 – 6 | 2 – 8 | Failed to make playoffs |
Henlopen Southern Division
| School | Team | Division Record | Overall record | Season Outcome |
| Delmar | Wildcats | 6 – 0 | 10 – 1 | Loss in semifinals of Div. II playoffs |
| Indian River | Indians | 5 – 1 | 8 – 3 | Loss in first round of Div. II playoffs |
| Milford | Buccaneers | 4 – 2 | 6 – 4 | Failed to make playoffs |
| Woodbridge | Blue Raiders | 3 – 3 | 4 – 6 | Failed to make playoffs |
| Laurel | Bulldogs | 2 – 4 | 5 – 5 | Failed to make playoffs |
| Lake Forest | Spartans | 1 – 5 | 1 – 9 | Failed to make playoffs |
| Seaford | Blue Jays | 0 – 6 | 1 – 9 | Failed to make playoffs |

##### 2008 Regular season Football Standings

Henlopen Northern Division
| School | Team | Division Record | Overall record | Season Outcome |
| Sussex Central | Golden Knights | 6 – 0 | 10 – 2 | Loss in Div. I Championship Game |
| Caesar Rodney | Riders | 5 – 1 | 11 – 1 | Won Div. I State Championship |
| Dover | Senators | 4 – 2 | 6 – 4 | Failed to make playoffs |
| Smyrna | Eagles | 2 – 4 | 5 – 5 | Failed to make playoffs |
| Sussex Tech | Ravens | 2 – 4 | 4 – 6 | Failed to make playoffs |
| Cape Henlopen | Vikings | 2 – 4 | 3 – 7 | Failed to make playoffs |
| Polytech | Panthers | 0 – 6 | 2 – 8 | Failed to make playoffs |
Henlopen Southern Division
| School | Team | Division Record | Overall record | Season Outcome |
| Milford | Buccaneers | 5 – 1 | 10 – 2 | Won Div. II State Championship |
| Laurel | Bulldogs | 5 – 1 | 9 – 3 | Loss in Div. II State Championship Game |
| Indian River | Indians | 4 – 2 | 7 – 4 | Loss in first round of Div. II playoffs |
| Delmar | Wildcats | 4 – 2 | 8 – 2 | Failed to make playoffs |
| Seaford | Blue Jays | 2 – 4 | 2 – 8 | Failed to make playoffs |
| Lake Forest | Spartans | 1 – 5 | 3 – 7 | Failed to make playoffs |
| Woodbridge | Blue Raiders | 0 – 6 | 0 – 10 | Failed to make playoffs |
The week one meeting between Milford and St. Marks (Wilmington, Delaware) was ranked the #10 matchup in the nation by MaxPreps.

##### 2009 Regular season Football Standings

Henlopen Northern Division
| School | Team | Division Record | Overall record | Season Outcome |
| Sussex Tech | Ravens | 5 – 1 | 9 – 2 | Loss in first round of Div. I playoffs |
| Caesar Rodney | Riders | 5 – 1 | 8 – 4 | Loss in semifinals of Div. I playoffs |
| Milford | Buccaneers | 5 – 1 | 6 – 4 | Failed to make playoffs |
| Sussex Central | Golden Knights | 2 – 4 | 6 – 4 | Failed to make playoffs |
| Dover | Senators | 2 – 4 | 4 – 6 | Failed to make playoffs |
| Smyrna | Eagles | 2 – 4 | 2 – 8 | Failed to make playoffs |
| Cape Henlopen | Vikings | 0 – 6 | 1 – 9 | Failed to make playoffs |
Henlopen Southern Division
| School | Team | Division Record | Overall record | Season Outcome |
| Delmar | Wildcats | 6 – 0 | 10 – 3 | Won Div. II State Championship |
| Laurel | Bulldogs | 5 – 1 | 8 – 3 | Loss in semifinals of Div. II playoffs |
| Lake Forest | Spartans | 4 – 2 | 7 – 3 | Failed to make playoffs |
| Indian River | Indians | 3 – 3 | 5 – 5 | Failed to make playoffs |
| Seaford | Blue Jays | 2 – 4 | 4 – 6 | Failed to make playoffs |
| Polytech | Panthers | 1 – 5 | 1 – 9 | Failed to make playoffs |
| Woodbridge | Blue Raiders | 0 – 6 | 3 – 7 | Failed to make playoffs |

#### 2010s
##### 2010 Regular season Football Standings

Henlopen Northern Division
| School | Team | Division Record | Overall record | Season Outcome |
| Sussex Central | Golden Knights | 5 – 1 | 7 – 4 | Loss in first round of Div. I playoffs |
| Caesar Rodney | Riders | 5 – 1 | 7 – 4 | Loss in first round of Div. I playoffs |
| Dover | Senators | 3 – 3 | 6 – 4 | Failed to make playoffs |
| Sussex Tech | Ravens | 3 – 3 | 5 – 5 | Failed to make playoffs |
| Cape Henlopen | Vikings | 2 – 4 | 5 – 5 | Failed to make playoffs |
| Smyrna | Eagles | 2 – 4 | 4 – 6 | Failed to make playoffs |
| Milford | Buccaneers | 1 – 5 | 3 – 7 | Failed to make playoffs |
Henlopen Southern Division
| School | Team | Division Record | Overall record | Season Outcome |
| Lake Forest | Spartans | 5 – 1 | 8 – 3 | Loss in first round of Div. II playoffs |
| Delmar | Wildcats | 4 – 2 | 8 – 4 | Loss in semifinals of Div. II playoffs |
| Laurel | Bulldogs | 4 – 2 | 5 – 5 | Failed to make playoffs |
| Indian River | Indians | 4 – 2 | 5 – 5 | Failed to make playoffs |
| Polytech | Panthers | 3 – 3 | 4 – 6 | Failed to make playoffs |
| Woodbridge | Blue Raiders | 1 – 5 | 3 – 7 | Failed to make playoffs |
| Seaford | Blue Jays | 0 – 6 | 2 – 8 | Failed to make playoffs |

##### 2011 Regular season Football Standings

Henlopen Northern Division
| School | Team | Division Record | Overall record | Season Outcome |
| Sussex Central | Golden Knights | 6 – 0 | 7 – 4 | Loss in first round of Div. I playoffs |
| Dover | Senators | 5 – 1 | 8 – 4 | Loss in semifinals of Div. I playoffs |
| Cape Henlopen | Vikings | 4 – 2 | 8 – 2 | Failed to make playoffs |
| Caesar Rodney | Riders | 3 – 3 | 3 – 7 | Failed to make playoffs |
| Smyrna | Eagles | 2 – 4 | 5 – 5 | Failed to make playoffs |
| Sussex Tech | Ravens | 1 – 5 | 4 – 6 | Failed to make playoffs |
| Milford | Buccaneers | 0 – 6 | 1 – 9 | Failed to make playoffs |
Henlopen Southern Division
| School | Team | Division Record | Overall record | Season Outcome |
| Indian River | Indians | 6 – 0 | 12 – 0 | Won Div. II State Championship |
| Delmar | Wildcats | 5 – 1 | 9 – 2 | Loss in first round of Div. II playoffs |
| Laurel | Bulldogs | 4 – 2 | 4 – 6 | Failed to make playoffs |
| Lake Forest | Spartans | 3 – 3 | 5 – 5 | Failed to make playoffs |
| Polytech | Panthers | 2 – 4 | 2 – 8 | Failed to make playoffs |
| Woodbridge | Blue Raiders | 1 – 5 | 2 – 8 | Failed to make playoffs |
| Seaford | Blue Jays | 0 – 6 | 0 – 10 | Failed to make playoffs |

##### 2012 Regular season Football Standings

Henlopen Northern Division
| School | Team | Division Record | Overall record | Season Outcome |
| Sussex Central | Golden Knights | 5 – 1 | 8 – 3 | Loss in first round of Div. I playoffs |
| Cape Henlopen | Vikings | 5 – 1 | 8 – 3 | Loss in first round of Div. I playoffs |
| Caesar Rodney | Riders | 5 – 1 | 8 – 4 | Loss in semi-finals of Div. I playoffs |
| Dover | Senators | 3 – 3 | 5 – 5 | Failed to make playoffs |
| Sussex Tech | Ravens | 2 – 4 | 3 – 7 | Failed to make playoffs |
| Smyrna | Eagles | 1 – 5 | 4 – 6 | Failed to make playoffs |
| Milford | Buccaneers | 0 – 6 | 3 – 7 | Failed to make playoffs |
Henlopen Southern Division
| School | Team | Division Record | Overall record | Season Outcome |
| Indian River | Indians | 6 – 0 | 9 – 3 | Loss in semi-finals of Div. II playoffs |
| Delmar | Wildcats | 5 – 1 | 7 – 3 | Failed to make playoffs |
| Lake Forest | Spartans | 4 – 2 | 5 – 5 | Failed to make playoffs |
| Laurel | Bulldogs | 3 – 3 | 4 – 6 | Failed to make playoffs |
| Woodbridge | Blue Raiders | 2 – 4 | 2 – 8 | Failed to make playoffs |
| Seaford | Blue Jays | 1 – 5 | 1 – 9 | Failed to make playoffs |
| Polytech | Panthers | 0 – 6 | 1 – 9 | Failed to make playoffs |

##### 2013 Regular season Football Standings

Henlopen Northern Division
| School | Team | Division Record | Overall record | Season Outcome |
| Caesar Rodney | Riders | 6 – 0 | 8 – 4 | Loss in semi-finals of Div. I playoffs |
| Dover | Senators | 5 – 1 | 9 – 3 | Loss in semi-finals of Div. I playoffs |
| Cape Henlopen | Vikings | 4 – 2 | 6 – 4 | Failed to make playoffs |
| Sussex Tech | Ravens | 3 – 3 | 5 – 5 | Failed to make playoffs |
| Sussex Central | Golden Knights | 2 – 4 | 5 – 5 | Failed to make playoffs |
| Polytech | Panthers | 1 – 5 | 5 – 5 | Failed to make playoffs |
| Smyrna | Eagles | 0 – 6 | 2 – 8 | Failed to make playoffs |
Henlopen Southern Division
| School | Team | Division Record | Overall record | Season Outcome |
| Indian River | Indians | 5 – 1 | 6 – 5 | Loss in first round of Div. II playoffs |
| Delmar | Wildcats | 5 – 1 | 9 – 2 | Loss in first round of Div. II playoffs |
| Woodbridge | Blue Raiders | 4 – 2 | 8 – 4 | Loss in semi-finals of Div. II playoffs |
| Lake Forest | Spartans | 4 – 2 | 6 – 4 | Failed to make playoffs |
| Laurel | Bulldogs | 2 – 4 | 2 – 8 | Failed to make playoffs |
| Milford | Buccaneers | 1 – 5 | 1 – 9 | Failed to make playoffs |
| Seaford | Blue Jays | 0 – 6 | 3 – 7 | Failed to make playoffs |

##### 2014 Regular season Football Standings

Henlopen Northern Division
| School | Team | Division Record | Overall record | Season Outcome |
| Sussex Tech | Ravens | 6 – 0 | 10 – 2 | Loss in semifinals of Div. I playoffs |
| Cape Henlopen | Vikings | 4 – 2 | 8 – 2 | Failed to make playoffs |
| Smyrna | Eagles | 3 – 3 | 5 – 5 | Failed to make playoffs |
| Sussex Central | Golden Knights | 3 – 3 | 5 – 5 | Failed to make playoffs |
| Caesar Rodney | Riders | 2 – 4 | 2 – 8 | Failed to make playoffs |
| Dover | Senators | 2 - 4 | 3 - 7 | Failed to make playoffs |
| Polytech | Panthers | 1 – 5 | 4 – 6 | Failed to make playoffs |
Henlopen Southern Division
| School | Team | Division Record | Overall record | Season Outcome |
| Lake Forest | Spartans | 6 – 0 | 10 – 1 | Loss in first round of Div. II playoffs |
| Laurel | Bulldogs | 5 – 1 | 10 – 3 | Loss in Div. II Championship Game |
| Delmar | Wildcats | 4 – 2 | 5 – 5 | Failed to make playoffs |
| Indian River | Indians | 3 - 3 | 4 - 6 | Failed to make playoffs |
| Woodbridge | Blue Raiders | 2 – 4 | 4 – 6 | Failed to make playoffs |
| Milford | Buccaneers | 1 – 5 | 1 – 9 | Failed to make playoffs |
| Seaford | Blue Jays | 0 – 6 | 1 – 9 | Failed to make playoffs |

##### 2015 Regular season Football Standings

Henlopen Northern Division
| School | Team | Division Record | Overall record | Season Outcome |
| Smyrna | Eagles | 6 – 0 | 12 – | Won Div. I State Championship |
| Sussex Tech | Ravens | 5 – 1 | 8 – 3 | Loss in first round of Div. I playoffs |
| Sussex Central | Golden Knights | 4 – 2 | 6 – 4 | Failed to make playoffs |
| Cape Henlopen | Vikings | 3 – 3 | 5 – 4 | Failed to make playoffs |
| Dover | Senators | 2 – 4 | 4 – 6 | Failed to make playoffs |
| Caesar Rodney | Riders | 1 - 5 | 2 - 8 | Failed to make playoffs |
| Polytech | Panthers | 0 – 6 | 0 – 10 | Failed to make playoffs |
Henlopen Southern Division
| School | Team | Division Record | Overall record | Season Outcome |
| Lake Forest | Spartans | 6 – 0 | 8 – 3 | Loss in first round of Div. II playoffs |
| Woodbridge | Blue Raiders | 5 – 1 | 8 – 4 | Loss in semifinals of Div. II playoffs |
| Indian River | Indians | 4 – 2 | 4 – 6 | Failed to make playoffs |
| Milford | Buccaneers | 3 - 3 | 6 - 4 | Failed to make playoffs |
| Laurel | Bulldogs | 2 – 4 | 3 – 7 | Failed to make playoffs |
| Delmar | Wildcats | 1 – 5 | 1 – 9 | Failed to make playoffs |
| Seaford | Blue Jays | 0 – 6 | 0 – 10 | Failed to make playoffs |

### Henlopen Conference Football Championships (By Year)

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.

### Total Henlopen Conference Football Championships

| School | Division | Total | Notes |
| Caesar Rodney | North | 19 | Most all time in Northern Division |
| Cape Henlopen | North | 7 | Includes two wins by Rehoboth |
| Delmar | South | 14 | |
| Dover | North | 6 | |
| Dover AF | n/a | 1 | defunct |
| Indian River | South | 16 | Includes two won by John M Clayton – Most all time in the Southern Division |
| Lake Forest | South | 10 | Includes one won by Harrington |
| Laurel | South | 4 | |
| Milford | North | 2 | One in the North; One in the South |
| Polytech | South | 0 | |
| Seaford | South | 9 | Six in the North; Three in the South |
| Smyrna | North | 9 | Four in the North; Five in the South |
| Sussex Central | North | 11 | Includes two won by Millsboro |
| Sussex Tech | North | 2 | |
| Woodbridge | South | 6 | Includes three won by Bridgeville |

### Football rivalries

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)

## Wrestling championships

| Year | Henlopen South | Henlopen North | Conference Dual Meet | Tournament champion |
| 2011-12 | Polytech | Caesar Rodney | No longer awarded | Caesar Rodney |
| 2010-11 | Seaford, Polytech, Indian River | Sussex Central | No longer awarded | Caesar Rodney |
| 2009-10 | | Sussex Central | No longer awarded | Sussex Central |
| 2008-09 | Milford | Caesar Rodney | Caesar Rodney | Smyrna |
| 2007-08 | Indian River | Sussex Central | Sussex Central | Sussex Central |
| 2006-07 | | Caesar Rodney | Caesar Rodney | Caesar Rodney |
| 2005-06 | | Caesar Rodney | Caesar Rodney | Caesar Rodney |
| 2004-05 | Milford | | Sussex Central | Sussex Central |
| 2003-04 | Laurel | Caesar Rodney | Sussex Central | Sussex Central |
| 2002-03 | Smyrna | Caesar Rodney | Caesar Rodney | Sussex Central |
| 2001-02 | Lake Forest | Caesar Rodney | Caesar Rodney | Sussex Central |
| 2000-01 | Milford | Caesar Rodney | Caesar Rodney | Caesar Rodney |
| 1999-00 | Milford | Caesar Rodney | Caesar Rodney | Caesar Rodney |
| 1998 | Smyrna | Caesar Rodney | Caesar Rodney | Caesar Rodney |
| 1997 | Smyrna | Caesar Rodney | Caesar Rodney | Caesar Rodney |
| 1996 | Smyrna | Caesar Rodney | Caesar Rodney | Caesar Rodney |
| 1995 | Smyrna | Sussex Central | Smyrna | Smyrna |
| 1994 | Smyrna | Dover | Dover | Dover |
| 1993 | Smyrna | Dover | Dover | Dover |
| 1992 | Smyrna | Dover | Dover | Dover |
| 1991 | Smyrna | Dover | Smyrna | Dover |
| 1990 | Smyrna | Cape Henlopen | Smyrna | Smyrna |
| 1989 | Smyrna | Sussex Central | Smyrna | Smyrna |
| 1988 | Smyrna | Dover | Dover | Dover |
| 1987 | Smyrna | Dover | Smyrna | Dover |
| 1986 | Smyrna | Dover | Smyrna | Dover |
| 1985 | Smyrna | Caesar Rodney | Caesar Rodney | Caesar Rodney |
| 1984 | Smyrna | Caesar Rodney | Caesar Rodney | Caesar Rodney |
| 1983 | Laurel | Caesar Rodney | Caesar Rodney | Caesar Rodney |
| 1982 | Smyrna | Caesar Rodney | Caesar Rodney | Caesar Rodney |
| 1981 | Smyrna | Milford | Milford | None |
| 1980 | Smyrna | Milford | Milford | None |
| 1979 | Smyrna | Caesar Rodney | Smyrna | None |
| 1978 | Smyrna | Caesar Rodney | Smyrna | None |
| 1977 | Smyrna | Caesar Rodney | Caesar Rodney | None |
| 1976 | Smyrna | Sussex Central | Sussex Central | None |
| 1975 | Smyrna | Sussex Central | Smyrna | None |
| 1974 | Smyrna | Caesar Rodney | Caesar Rodney | None |
| 1973 | Smyrna | Caesar Rodney | Caesar Rodney | None |
| 1972 | Smyrna | Caesar Rodney | Smyrna, Caesar Rodney, Sussex Central | None |
| 1971 | Smyrna | Sussex Central | Smyrna | None |
| 1970 | Smyrna | Sussex Central | Smyrna | None |
| 1969 | None | None | None | Harrington |
| 1968 | None | None | None | ? |
| 1967 | None | None | None | Delmar |
| 1966 | None | None | None | Harrington |
| 1965 | None | None | None | Delmar |
| 1964 | None | None | None | Millsboro |
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

## Boys basketball championships

| Year | Henlopen South Division | Henlopen North Division | Conference Championship Game | Conference Champion |
| 2016-17 | Woodbridge | Smyrna | Smyrna 61 - Woodbridge 51 | Smyrna |
| 2015-16 | | | | |
| 2014-15 | | | | |
| 2013-14 Woodbridge Boys Henlopen Conference Championship Beat Caesar Rodney | | | | |
| 2012-13 | | | | |
| 2011-12 | | Smyrna | | |
| 2010-11 | Polytech | Smyrna | Smyrna 46 – Polytech 41 | Smyrna |
| 2009-10 | Polytech | Dover | Dover 71 – Polytech 55 | Dover |
| 2008-09 | Woodbridge | Caesar Rodney | Caesar Rodney 41 – Woodbridge 35 | Caesar Rodney |
| 2007-08 | Woodbridge | Sussex Central | Woodbridge 71 – Sussex Central 60 | Woodbridge |
| 2006-07 | | | | |
| 2005-06 | Smyrna | Cape Henlopen | Cape Henlopen 77 – Smyrna 52 | Cape Henlopen |
| 2004-05 | | | | |
| 2003 | | | | |
| 2002 | Lake Forest | Sussex Tech | Sussex Tech 58 – Lake Forest 48 | Sussex Tech |
| 2001 | Lake Forest | Sussex Central | Sussex Central 59 – Lake Forest 49 | Sussex Central |
| 2000 | Lake Forest | Sussex Tech | Sussex Tech 73 – Lake Forest 62 | Sussex Tech |
| 1999 | Lake Forest | Sussex Tech | Sussex Tech 63 – Lake Forest 50 | Sussex Tech |
| 1998 | Indian River | Cape Henlopen | Cape Henlopen 77 – Indian River 64 | Cape Henlopen |
| 1997 | Lake Forest | Cape Henlopen | Lake Forest 49 – Cape Henlopen 45 | Lake Forest |
| 1996 | Indian River | Cape Henlopen | Indian River 74 – Cape Henlopen 72 | Indian River |
| 1995 | Indian River | Cape Henlopen | Indian River 52 – Cape Henlopen 51 | Indian River |
| 1994 | Indian River | Caesar Rodney | Caesar Rodney 67 – Indian River 65 | Caesar Rodney |
| 1993 | Indian River | Sussex Central | Indian River 58 – Sussex Central 45 | Indian River |
| 1992 | Lake Forest | Dover | Dover 53 – Lake Forest 48 | Dover |
| 1991 | Indian River | Seaford | Indian River 69 – Seaford 59 | Indian River |
| 1990 | Indian River | Seaford | Indian River 65 – Seaford 63 | Indian River |
| 1989 | Indian River | Milford | Milford 82 – Indian River 73 | Milford |
| 1988 | Woodbridge | Seaford | Seaford 61 – Woodbridge 50 | Seaford |
| 1987 | Woodbridge | Seaford | Seaford 77 – Woodbridge 63 | Seaford |
| 1986 | Smyrna | Seaford | Seaford 74 – Smyrna 66 | Seaford |
| 1985 | Smyrna | Sussex Central | Smyrna 64 – Sussex Central 55 | Smyrna |
| 1984 | Seaford | Caesar Rodney | Caesar Rodney 61 – Seaford 60 | Caesar Rodney |
| 1983 | Woodbridge | Cape Henlopen | Cape Henlopen 92 – Woodbridge 80 | Cape Henlopen |
| 1982 | Lake Forest | Cape Henlopen | Cape Henlopen 71 – Lake Forest 57 | Cape Henlopen |
| 1981 | Indian River | Cape Henlopen | Cape Henlopen 67 – Indian River 66 | Cape Henlopen |
| 1980 | Indian River | Cape Henlopen | Cape Henlopen 77 – Indian River 63 | Cape Henlopen |
| 1979 | Indian River | Cape Henlopen | Cape Henlopen 49 – Indian River 36 | Cape Henlopen |
| 1978 | Indian River | Dover | Dover 55 – Indian River 53 | Dover |
| 1977 | Indian River | Dover | Dover 61 – Indian River 59 | Dover |
| 1976 | Indian River | Cape Henlopen | Cape Henlopen 78 – Indian River 57 | Cape Henlopen |
| 1975 | Indian River | Cape Henlopen | Cape Henlopen 64 – Indian River 52 | Cape Henlopen |
| 1974 | Indian River | Cape Henlopen | Indian River 66 – Cape Henlopen 62 | Indian River |
| 1973 | Woodbridge | Cape Henlopen | Woodbridge 63 – Cape Henlopen 62 | Woodbridge |
| 1972 | Indian River | Dover | Dover 69 – Indian River 53 | Dover |
| 1971 | Indian River | Milford | Milford 47 – Indian River 45 | Milford |
| 1970 | Lake Forest | Milford | Lake Forest 69 – Milford 43 | Lake Forest |
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

## Baseball championships

| Year | Henlopen South Division | Henlopen North Division | Conference Champion |
| 2009 | Milford | Sussex Central | Sussex Central |
| 2008 | Indian River | Sussex Central | Indian River |
| 2007 | Indian River | Caesar Rodney | Caesar Rodney |
| 2006 | Indian River | Cape Henlopen | Cape Henlopen |
| 2005 | Indian River | Cape Henlopen | ???? |
| 2004 | Delmar | Caesar Rodney | Caesar Rodeny |
| 2003 | Laurel | Cape Henlopen | Cape Henlopen |
| 2002 | Seaford | Sussex Central | Seaford |
| 2001 | Seaford | Caesar Rodney | Caesar Rodney |
| 2000 | Laurel | Sussex Central |

## Boys State Championships

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.

### Baseball

| Div I/Div II | School | Year |
| I/II | Dover Senators | 1972 |
| I/II | Caesar Rodney Riders | 1975 |
| I/II | Seaford Blue Jays | 1980 |
| I/II | Seaford Blue Jays | 1983 |
| I/II | Seaford Blue Jays | 1986 |
| I/II | Sussex Central Golden Knights | 1989 |
| I/II | Seaford Blue Jays | 1993 |
| I/II | Cape Henlopen Vikings | 2018 |

### Basketball

| Div I/Div II | School | Year |
| I/II | Milford Buccaneers | 1971 |
| I/II | Cape Henlopen Vikings | 1975 |
| I/II | Cape Henlopen Vikings | 1976 |
| I/II | Indian River Indians | 1980 |
| I/II | Indian River Indians | 1981 |
| I/II | Caesar Rodney Riders | 1984 |
| I/II | Seaford Blue Jays | 1997 |
| I/II | Smyrna Eagles | 2017 |

### Cross Country

| Div I/Div II | School | Year |
| II | Harrington Lions | 1963 |
| II | Harrington Lions | 1966 |
| II | Harrington Lions | 1969 |
| II | Dover Air Force Base Falcons | 1971 |
| II | Lake Forest Spartans | 1973 |
| II | Lake Forest Spartans | 1974 |
| II | Lake Forest Spartans | 1975 |
| II | Lake Forest Spartans | 1976 |
| II | Cape Henlopen Vikings | 1977 |
| II | Woodbridge Blue Raiders | 1978 |
| Div I/Div II | School | Year |
| II | Cape Henlopen Vikings | 1979 |
| II | Sussex Central Golden Knights | 1980 |
| II | Cape Henlopen Vikings | 1982 |
| II | Lake Forest Spartans | 1983 |
| II | Lake Forest Spartans | 1986 |
| II | Lake Forest Spartans | 1992 |
| II | Lake Forest Spartans | 1993 |
| II | Lake Forest Spartans | 1996 |
| II | Cape Henlopen Vikings | 1999 |
| II | Cape Henlopen Vikings | 2001 |
| Div I/Div II | School | Year |
| I | Cape Henlopen Vikings | 2020 |

### Football

| Div I/Div II | School | Year |
| I | Caesar Rodney Riders | 1975 |
| II | Delmar Wildcats | 1976 |
| I | Dover Senators | 1977 |
| I | Cape Henlopen Vikings | 1979 |
| I | Seaford Blue Jays | 1981 |
| II | Seaford Blue Jays | 1983 |
| II | Delmar Wildcats | 1985 |
| II | Laurel Bulldogs | 1986 |
| II | Laurel Bulldogs | 1987 |
| I | Dover Senators | 1988 |
| Div I/Div II | School | Year |
| II | Indian River Indians | 1988 |
| I | Caesar Rodney Riders | 1990 |
| II | Laurel Bulldogs | 1991 |
| II | Sussex Tech Ravens | 1993 |
| II | Lake Forest Spartans | 1995 |
| II | Delmar Wildcats | 2000 |
| II | Delmar Wildcats | 2001 |
| II | Delmar Wildcats | 2002 |
| I | Caesar Rodney Riders | 2008 |
| II | Milford Buccaneers | 2008 |
| Div I/Div II/Unified | School | Year |
| II | Delmar Wildcats | 2009 |
| II | Indian River Indians | 2011 |
| I | Smyrna Eagles | 2015 |
| I | Smyrna Eagles | 2016 |
| II | Woodbridge Blue Raiders | 2016 |
| I | Smyrna Eagles | 2017 |
| II | Delmar Wildcats | 2017 |
| I | Sussex Central Golden Knights | 2018 |
| II | Woodbridge Blue Raiders | 2018 |
| Unified | Smyrna Eagles | 2018 |
| Div I/Div II/Unified | School | Year |
| Unified | Dover Senators | 2019 |
| I | Sussex Central Golden Knights | 2020 |
* 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.

### Golf

| Div I/Div II | School | Year |
| I/II | Dover Senators | 1985 |
| I/II | Dover Senators | 1986 |
| I/II | Dover Senators | 1988 |
| I/II | Dover Senators | 1989 |
| I/II | Caesar Rodney Riders | 1990 |
| I/II | Dover Senators | 1991 |
| I/II | Dover Senators | 1992 |
| I/II | Dover Senators | 1993 |
| I/II | Dover Senators | 1994 |
| I/II | Dover Senators | 1995 |
| Div I/Div II | School | Year |
| I/II | Dover Senators | 1996 |
| I/II | Dover Senators | 1997 |
| I/II | Caesar Rodney Riders | 1998 |
| I/II | Dover Senators | 1999 |
| I/II | Dover Senators | 2000 |
| I/II | Dover Senators | 2003 |
| I/II | Caesar Rodney Riders | 2011 |
| I/II | Caesar Rodney Riders | 2012 |
| I/II | Caesar Rodney Riders | 2013 |

### Indoor Track

| Div I/Div II | School | Year |
| I/II | Cape Henlopen Vikings | 1984 |
| I/II | Cape Henlopen Vikings | 1985 |
| I/II | Seaford Blue Jays | 1991 |
| I/II | Cape Henlopen Vikings | 1993 |
| I/II | Dover Senators | 1995 |
| I/II | Dover Senators | 1998 |
| I/II | Dover Senators | 2002 |
| I/II | Caesar Rodney Riders | 2013 |
| I/II | Dover Senators | 2015 |
| I/II | Dover Senators | 2019 |

### Lacrosse

| Div I/Div II | School | Year |
| I/II | Caesar Rodney Riders | 1996 |
| I/II | Caesar Rodney Riders | 1997 |
| I/II | Cape Henlopen Vikings | 1998 |
| I/II | Caesar Rodney Riders | 1999 |
| I/II | Cape Henlopen Vikings | 2001 |
| I/II | Cape Henlopen Vikings | 2002 |
| I/II | Cape Henlopen Vikings | 2006 |
| I/II | Cape Henlopen Vikings | 2008 |
| I/II | Cape Henlopen Vikings | 2014 |
| I/II | Cape Henlopen Vikings | 2019 |

### Outdoor Track

| Div I/Div II | School | Year |
| I | Seaford Blue Jays | 1965 |
| I | Dover Senators | 1969 |
| I | Cape Henlopen Vikings | 1971 |
| I | Cape Henlopen Vikings | 1972 |
| I | Cape Henlopen Vikings | 1973 |
| I | Cape Henlopen Vikings | 1975 |
| I | Dover Senators | 1975 |
| II | Cape Henlopen Vikings | 1976 |
| I | Dover Senators | 1976 |
| I** | Dover Senators | 1977 |
| Div I/Div II | School | Year |
| II** | Seaford Blue Jays | 1977 |
| II | Cape Henlopen Vikings | 1978 |
| II | Woodbridge Blue Raiders | 1979 |
| I | Dover Senators | 1980 |
| II | Woodbridge Blue Raiders | 1981 |
| II | Woodbridge Blue Raiders | 1982 |
| II | Lake Forest Spartans | 1984 |
| I | Cape Henlopen Vikings | 1986 |
| II | Milford Buccaneers | 1986 |
| II | Lake Forest Spartans | 1987 |
| Div I/Div II | School | Year |
| II | Smyrna Eagles | 1990 |
| II | Smyrna Eagles | 1991 |
| II | Cape Henlopen Vikings | 1992 |
| II | Cape Henlopen Vikings | 1993 |
| I | Dover Senators | 1995 |
| II | Cape Henlopen Vikings | 2000 |
| II | Cape Henlopen Vikings | 2002 |
| I | Dover Senators | 2004 |
| II | Milford Buccaneers | 2005 |
| II | Milford Buccaneers | 2009 |
| Div I/Div II/Unified | School | Year |
| II | Milford Buccaneers | 2011 |
| I | Caesar Rodney Riders | 2013 |
| I | Caesar Rodney Riders | 2014 |
| I | Dover Senators | 2015 |
| II | Lake Forest Spartans | 2015 |
| Unified | Smyrna Eagles | 2016 |
| I | Dover Senators | 2017 |
| Unified | Caesar Rodney Riders | 2017 |
| I | Dover Senators | 2018 |
| Unified | Caesar Rodney Riders | 2018 |
* 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.

### Soccer

| Div I/Div II | School | Year |
| I/II | Caesar Rodney Riders | 1994 |
| II | Indian River Indians | 2013 |
| II | Indian River Indians | 2015 |
* 2013 was the first year that soccer was split into two state championships.

### Tennis

| Div I/Div II | School | Year |
| I/II | Caesar Rodney Riders | 2001 |
| I/II | Caesar Rodney Riders | 2005 |
| I/II | Caesar Rodney Riders | 2011 |
| I/II | Caesar Rodney Riders | 2012 |
| I/II | Caesar Rodney Riders | 2014 |
| I/II | Caesar Rodney Riders | 2015 |
| I/II | Caesar Rodney Riders | 2016 |
| I/II | Caesar Rodney Riders | 2018 |

### Wrestling

| Div I/Div II | School | Year |
| I/II | Caesar Rodney Riders | 1975 |
| I/II | Caesar Rodney Riders | 1978 |
| I/II | Caesar Rodney Riders | 1979 |
| I/II | Milford Buccaneers | 1980 |
| I/II | Milford Buccaneers | 1981 |
| I/II | Caesar Rodney Riders | 1982 |
| I/II | Caesar Rodney Riders | 1985 |
| II | Smyrna Eagles | 1993 |
| II | Smyrna Eagles | 1994 |
| II | Smyrna Eagles | 1996 |
| Div I/Div II | School | Year |
| I | Caesar Rodney Riders | 2001 |
| I | Caesar Rodney Riders | 2003 |
| II | Smyrna Eagles | 2003 |
| I | Caesar Rodney Riders | 2004 |
| II | Milford Buccaneers | 2004 |
| I | Caesar Rodney Riders | 2005 |
| II | Smyrna Eagles | 2005 |
| I | Caesar Rodney Riders | 2006 |
| I | Caesar Rodney Riders | 2007 |
| I | Sussex Central Golden Knights | 2008 |
| Div I/Div II | School | Year |
| II | Milford Buccaneers | 2009 |
| I | Sussex Central Golden Knights | 2010 |
| I | Caesar Rodney Riders | 2011 |
| I | Caesar Rodney Riders | 2012 |
| II | Polytech Panthers | 2012 |
| I | Smyrna Eagles | 2013 |
| I | Smyrna Eagles | 2014 |
| II | Milford Buccaneers | 2014 |
| I | Smyrna Eagles | 2015 |
| II | Milford Buccaneers | 2015 |
| Div I/Div II | School | Year |
| I | Smyrna Eagles | 2016 |
| II | Milford Buccaneers | 2016 |
| I | Sussex Central Golden Knights | 2017 |
| II | Milford Buccaneers | 2017 |
| I | Caesar Rodney Riders | 2018 |
| II | Milford Buccaneers | 2018 |
| I | Smyrna Eagles | 2019 |
| II | Milford Buccaneers | 2019 |
| I | Smyrna Eagles | 2020 |
| I | Cape Henlopen Vikings | 2021 |
* 1993 was the first year Wrestling was split into two state championships.

## Total Boys State Championships

| School | Baseball | Basketball | Cross Country | Football | Golf | Indoor Track | Lacrosse | Outdoor Track | Soccer | Tennis | Wrestling | School Totals |
| Caesar Rodney | 1 | 1 | 0 | 3 | 5 | 1 | 3 | 4 | 1 | 8 | 14 | 41 |
| Cape Henlopen | 1 | 2 | 6 | 1 | 0 | 3 | 7 | 11 | 0 | 0 | 1 | 32 |
| Dover | 1 | 0 | 0 | 3 | 14 | 5 | 0 | 10 | 0 | 0 | 0 | 33 |
| Lake Forest | 0 | 0 | 12 | 1 | 0 | 0 | 0 | 3 | 0 | 0 | 0 | 16 |
| Milford | 0 | 1 | 0 | 1 | 0 | 0 | 0 | 4 | 0 | 0 | 10 | 16 |
| Smyrna | 0 | 1 | 0 | 4 | 0 | 0 | 0 | 3 | 0 | 0 | 11 | 19 |
| Seaford | 4 | 1 | 0 | 2 | 0 | 1 | 0 | 2 | 0 | 0 | 0 | 10 |
| Delmar | 0 | 0 | 0 | 7 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 7 |
| Indian River | 0 | 2 | 0 | 2 | 0 | 0 | 0 | 0 | 2 | 0 | 0 | 6 |
| Woodbridge | 0 | 0 | 1 | 2 | 0 | 0 | 0 | 3 | 0 | 0 | 0 | 6 |
| Sussex Central | 1 | 0 | 1 | 2 | 0 | 0 | 0 | 0 | 0 | 0 | 3 | 7 |
| Laurel | 0 | 0 | 0 | 3 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 3 |
| Polytech | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 1 | 1 |
| Sussex Tech | 0 | 0 | 0 | 1 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 1 |
| Dover Air Force* | 0 | 0 | 1 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 1 |
| Conference Totals | 8 | 8 | 21 | 31 | 19 | 10 | 10 | 40 | 3 | 8 | 39 | 197 |
* Dover Air Force Base High School shut down operations in the mid-1980s and students were absorbed into Caesar Rodney .

## Girls State Championships

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.

### Basketball

| Div I/Div II | School | Year |
| I/II | Cape Henlopen Vikings | 1973 |
| I/II | Polytech Panthers | 2003 |
* Cape Henlopen won the first girls basketball championship in 1973.

### Cross Country

| Div I/Div II | School | Year |
| II | Lake Forest Spartans | 1990 |
| II | Lake Forest Spartans | 1993 |
| II | Cape Henlopen Vikings | 1999 |
| II | Seaford Blue Jays | 2000 |
| I | Caesar Rodney Riders | 2001 |
| I | Caesar Rodney Riders | 2002 |
| II | Lake Forest Spartans | 2002 |

### Field Hockey

| Div I/Div II | School | Year |
| I/II | Cape Henlopen Vikings | 1979 |
| I/II | Cape Henlopen Vikings | 1995 |
| I/II | Milford Buccaneers | 1996 |
| I/II | Caesar Rodney Riders | 2004 |
| I/II | Sussex Tech Ravens | 2009 |
| I/II | Sussex Tech Ravens | 2010 |
| I/II | Cape Henlopen Vikings | 2011 |
| I/II | Cape Henlopen Vikings | 2012 |
| I/II | Cape Henlopen Vikings | 2013 |
| I/II | Cape Henlopen Vikings | 2014 |
| I/II | Cape Henlopen Vikings | 2015 |
| I/II | Delmar Wildcats | 2016 |
| I | Cape Henlopen Vikings | 2017 |
| II | Delmar Wildcats | 2017 |
| I | Cape Henlopen Vikings | 2018 |
| II | Delmar Wildcats | 2018 |
| I | Cape Henlopen Vikings | 2019 |
| II | Delmar Wildcats | 2019 |
| I | Cape Henlopen Vikings | 2020 |
| II | Delmar Wildcats | 2020 |
* 2017 was the first year of a split between Division 1 and Division 2, with separate state championships

### Indoor Track

| Div I/Div II | School | Year |
| I/II | Dover Senators | 1992 |
| I/II | Dover Senators | 1993 |
| I/II | Dover Senators | 1995 |
| I/II | Dover Senators | 2000 |

### Lacrosse

| Div I/Div II | School | Year |
| I/II | Cape Henlopen Vikings | 2009 |
| I/II | Cape Henlopen Vikings | 2010 |
| I/II | Cape Henlopen Vikings | 2011 |
| I/II | Cape Henlopen Vikings | 2012 |
| I/II | Cape Henlopen Vikings | 2013 |
| I/II | Cape Henlopen Vikings | 2014 |
| I/II | Cape Henlopen Vikings | 2015 |
| I/II | Cape Henlopen Vikings | 2016 |
* 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.

### Outdoor Track

| Div I/Div II | School | Year |
| I/II | Dover Senators | 1973 |
| I South | Caesar Rodney Riders | 1977 |
| I | Caesar Rodney Riders | 1978 |
| I | Caesar Rodney Riders | 1979 |
| I | Caesar Rodney Riders | 1980 |
| II | Lake Forest Spartans | 1983 |
| II | Seaford Blue Jays | 1984 |
| II | Seaford Blue Jays | 1985 |
| II | Seaford Blue Jays | 1986 |
| I | Dover Senators | 1993 |
| I | Dover Senators | 1994 |
| I | Dover Senators | 1998 |
| I | Dover Senators | 1999 |
| I | Dover Senators | 2000 |
| I | Caesar Rodney Riders | 2001 |
| II | Lake Forest Spartans | 2001 |
| I | Caesar Rodney Riders | 2002 |
| II | Cape Henlopen Vikings | 2002 |
| II | Cape Henlopen Vikings | 2003 |
| II | Cape Henlopen Vikings | 2004 |
| II | Cape Henlopen Vikings | 2005 |
| II | Milford Buccaneers | 2006 |
| I | Cape Henlopen Vikings | 2011 |
| I | Cape Henlopen Vikings | 2012 |
| I | Smyrna Eagles | 2013 |
* Dover won the first outdoor track championship in 1973.
* 1977 was the only year for a Division 1 North and Division 1 South outdoor track championship.

### Tennis

| Div I/Div II | School | Year |
| I/II | Seaford Blue Jays | 1991 |
| I/II | Cape Henlopen Vikings | 1991 |
| I/II | Seaford Blue Jays | 1992 |
| I/II | Milford Buccaneers | 1997 |
| I/II | Cape Henlopen Vikings | 2011 |
| I/II | Caesar Rodney Riders | 2016 |

### Softball

| Div I/Div II | School | Year |
| I/II | Milford Buccaneers | 1976 |
| I/II | Lake Forest Spartans | 1979 |
| I/II | Smyrna Eagles | 1993 |
| I/II | Sussex Central Golden Knights | 1995 |
| I/II | Indian River Indians | 1998 |
| I/II | Caesar Rodney Riders | 2003 |
| I/II | Sussex Central Golden Knights | 2005 |
| I/II | Sussex Tech Ravens | 2007 |
| I/II | Sussex Central Golden Knights | 2008 |
| I/II | Milford Buccaneers | 2009 |
| I/II | Sussex Tech Ravens | 2012 |
| I/II | Laurel Bulldogs | 2013 |
| I/II | Laurel Bulldogs | 2014 |
| I/II | Polytech Panthers | 2015 |
* Milford won the first softball championship in 1976.

## Total Girls State Championships

| School | Basketball | Cross Country | Field Hockey | Indoor Track | Lacrosse | Outdoor Track | Tennis | Softball | School Totals |
| Caesar Rodney | 0 | 2 | 1 | 0 | 0 | 6 | 1 | 1 | 11 |
| Cape Henlopen | 1 | 1 | 11 | 0 | 8 | 6 | 2 | 0 | 29 |
| Dover | 0 | 0 | 0 | 4 | 0 | 6 | 0 | 0 | 10 |
| Lake Forest | 0 | 3 | 0 | 0 | 0 | 2 | 0 | 1 | 6 |
| Milford | 0 | 0 | 1 | 0 | 0 | 1 | 1 | 2 | 5 |
| Seaford | 0 | 1 | 0 | 0 | 0 | 3 | 2 | 0 | 6 |
| Smyrna | 0 | 0 | 0 | 0 | 0 | 1 | 0 | 1 | 2 |
| Delmar | 0 | 0 | 5 | 0 | 0 | 0 | 0 | 0 | 5 |
| Indian River | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 1 | 1 |
| Woodbridge | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
| Laurel | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 2 | 2 |
| Sussex Central | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 3 | 3 |
| Polytech | 1 | 0 | 0 | 0 | 0 | 0 | 0 | 1 | 2 |
| Sussex Tech | 0 | 0 | 2 | 0 | 0 | 0 | 0 | 2 | 4 |
| Conference Totals | 2 | 7 | 12 | 4 | 8 | 25 | 6 | 14 | 78 |

## Overall state championships

The total number of state championships won by Henlopen Conference teams in both boys and girls sports, in order of championships won:
Cape Henlopen Vikings – 54 Caesar Rodney Riders – 48 Dover Senators – 37 Lake Forest Spartans – 22 Milford Buccaneers – 21 Seaford Blue Jays – 16 Smyrna Eagles – 15 Sussex Central Golden Knights – 10 Delmar Wildcats – 7 Indian River Indians – 7 Woodbridge Blue Raiders – 6 Laurel Bulldogs – 5 Sussex Tech Ravens – 5 Polytech Panthers – 3 Dover Air Force Base (defunct) – 1

## 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 (Dover Senators) played center and guard for the Brooklyn Dodgers football team of the All-America Football Conference (the precursor to today's American Football Conference in the National Football League) from 1946 to 1948 out of Auburn University.
* Carl Elliott of Laurel (Laurel Bulldogs) 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 to 1956, is one of only two players in Major League Baseball history to go 4 for 4 in his first major league game (the other being Delino DeShields of Seaford, Delaware), and is a 1991 inductee to the Delaware Sports Museum and Hall of Fame.
* 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.
* Carl Ergenzinger of Dover (Dover Senators) 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 (Milford Buccaneers) was a pitcher for the Houston Astros, making the team in a 1967 tryout.
* Thomas Sullivan of Dover (Dover Senators) was drafted as a pitcher in the eleventh round by the Cleveland Indians in 1969.
* Randy Lee of Laurel (Laurel Bulldogs) was drafted as a pitcher in the 15th round by the Baltimore Orioles in 1970.
* Renie Martin of Dover (Dover Senators) 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 (Dover Senators) was a pitcher drafted by the Oakland Athletics in the 33rd round of the 1978 draft.
* Randy Bush of Dover (Dover Senators) 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 (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.
* Mike Meade of Dover (Dover Senators) played fullback for the Green Bay Packers and Detroit Lions from 1982 to 1985 out of Pennsylvania State University.
* 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.
* Stoney Briggs of Seaford (Seaford Blue Jays) 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 (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.
* 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.
* Luke Petitgout of Georgetown (Sussex Central Golden Knights) 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 (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.
* Theodis Bowe of Ellendale (Milford Buccaneers) was drafted as a center fielder by the Cincinnati Reds in the 21st 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.
* 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.
* 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.
* Carrie Lingo of Rehoboth Beach (Cape Henlopen Vikings) 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.
* 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.