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.
Two weeks later, on February 3, 1959, the Harrington Lions and Felton Green Devils were admitted, expanding the league into Kent County.
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.
Since 1969, teams in the Henlopen Conference have won a total of 25 state football championships.
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 2006 Lake Forest High School had to temporarily shut down their varsity football team due to allegations of use of painkillers.
[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.
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.
Battle of the Bell Milford vs. Lake Forest – Started in 1969 when the conferences were formed and school districts were consolidated.
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) 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.
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
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.
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[32]