Prediction: Middletown (Del.) falls short in quest to repeat

The 2025 high school football season will be getting underway in less than six weeks, which means it’s officially preview season. Rivals is breaking down the nation’s top teams from coast-to-coast, and today we head to Delaware where the Middletown football team opens the season as the defending state champions. Can the Cavaliers overcome the departures of a strong class of graduated seniors and successfully defend their title?

Player Spotlight: QB Derian Cunningham

Derian Cunningham returns for his senior season after leading the Cavaliers to the DIAA state championship a year ago. He will have an experienced offensive group returning, including Temple commit Darius Pope at receiver and running back Amar’e Glover. Last season Cunningham threw for nearly 1,900 yards, 20 touchdowns and only four interceptions.

Others to watch: ATH Sy’Mir Queen, DB Dorian Rutledge, WR Darius Pope, RB Amar’e Glover

Season Prediction: 5-4

It’s usually a good thing, win or lose, to start off the season against a host of quality, out-of-state opponents. The early part of Middletown’s schedule includes games against Bishop Watterson (Ohio), Red Bank Catholic (N.J.) and Good Counsel (Md.), all powers in their respective states. In this case, a slow start will derail the Cavaliers’ chances to repeat as state champions. They’ll be unable to overcome a 0-3 start and will also drop a regular season game to Salesianum, who they faced in the state title game last fall.

Game-By-Game Predictions

Aug. 30 – at Bishop Watterson (Ohio) Eagles – L
Up against a Bishop Watterson team that went undefeated and won a state championship last year in Ohio, the Cavaliers come up short.

Sep. 5 – at Red Bank Catholic (N.J.) Caseys – L
Looking to bounce back, Middletown stays in it but Red Bank Catholic scores a late game-winner. The Cavaliers are off to a 0-2 start.

Sep. 12 – Good Counsel (Md.) Falcons – L
Up against a DMV power in the team’s home opener, the Cavaliers are overpowered and fall to 0-3.

Sep. 26 – Smyrna (Del.) Eagles – W
Coming out of a bye week, the Middletown football team pick-up its first win in a 20-point triumph over the Eagles.

Oct. 3 – at Sussex Central Senior (Del.) Golden Knights – W 
The Cavaliers go back on the road and defeat the Golden Knights by two scores.

Oct. 11 – at William Penn (Del.) Colonials – W
It looks like Middletown has found their groove offensively as the have the best offensive output of the season with 38 points and a third straight win.

Oct. 17 – Caravel Academy (Del.) Buccaneers – W
Four in a row and the Cavaliers look to be hitting on all cylinders heading into a DIAA state title rematch with Salesianum.

Oct. 24 – at Salesianum (Del.) Buccaneers – L

The four-game winning streak comes to a halt and Middletown falls to 4-3 on the season.

Nov. 1 – at Hodgson Vo-Tech (Del.) Eagles – W
Only way to get back on track is to win and that is exactly what the Cavs do in a 27-point victory.

Nov. 7 – Appoquinimink (Del.) Eagles – W
The Middletown football team ends the regular season with a feel good win at home and get over the .500 mark heading into the DIAA postseason.