Maryland’s 2026 high school football slate is packed with the kind of games that can tilt conference races, reshape playoff paths and shake up the statewide pecking order before the calendar even turns to November.
There are championship rematches, old rivalries and a few interstate tests sprinkled all over the schedule. If you’re circling only a handful of dates this fall, these are the ones worth the trip.
The season opens with a few games that should tell us plenty right away. One early matchup pits the Bulldogs, coached by Joe Rydzewski since 2021, against Matt Schwartzback’s Barons, who have become one of the more interesting programs in Montgomery County in recent seasons. That opener should offer an early read on both teams.
Another Week 1 game sends John Kelley’s Cougars to Ashburn for their annual meeting with the Virginia-based Bulldogs. Quince Orchard is coming off a 20-0 win in Gaithersburg last year, and the yearly crossover remains one of the most reliable fixtures on the schedule.
Also in the opening week, Messay Hailemariam’s Panthers will line up against the Florida-based Bulldogs. The Panthers were No. 1 in High School On SI’s Maryland Football Power 25 rankings in 2025 after finishing 9-1, while the Bulldogs went 13-1 last season.
The start of the year also brings a Baltimore City-versus-county matchup at Under Armour Stadium, where the Poets will meet the Millers. The Poets are coming off the 2025 MPSSAA 2A/1A state title, while the Millers reached the 3A semifinals.
A separate opening-week game features two state champions from last season: the Mustangs, who won the 4A/3A title, and the Lancers, who captured the 3A crown.
The first month also includes a trip to Annapolis for Dan Paro’s Little Hoyas, who open against the Saints and rising senior quarterback DJ Hitaffer.
Several September games carry plenty of weight too. The Cavaliers begin the month against the Cadets in the second of three WCAC matchups to start the year.
Robert “R.B” Green has taken over as head coach after Kyle Schmidt’s long run, so the Cavaliers will be adjusting as they move through that stretch. The next week, they head to Olney to face the Falcons in their third and final WCAC game to open 2026.
One of the more eye-catching early-season rivalries belongs to Broadneck and Annapolis. The Bruins have won the last 15 meetings against the Falcons, and a 16th would come on Halloween weekend. Rob Harris led Broadneck to the MPSSAA 4A state semifinals in 2025.
Prince George’s County gets its own spotlight when the Pumas meet the Raiders. Steve Rapp’s Pumas are coming off back-to-back trips to the MPSSAA 4A state title game, while the Raiders are fresh off a 7-3 season.
There’s also a major private-school milestone on the calendar: the 100th meeting in one of the nation’s most enduring rivalries. Gilman is back in the mix as a MIAA playoff team after last season, and while the Eagles have had the upper hand lately, Gilman still leads the all-time series 61-41.
October is loaded with rematches and rivalry games. One of them sends the Bulldogs against the Falcons in a home game that should draw plenty of attention, even without Georgetown Prep on the Bulldogs’ regular-season schedule. The Falcons will have a new coach in Sal Gorgone, who takes over for Andy Stefanelli.
Another October clash has the Cougars and Bulldogs meeting again, and John Kelley’s team has controlled the series so far, winning all four previous matchups.
The WCAC also gets a title-game rematch when the Knights visit the Panthers in Chantilly. The Knights are the defending WCAC Metro champions and will be looking to keep that momentum rolling.
Good Counsel will also see a familiar face return in a new role. Andy Stefanelli is back with the program as the Cadets’ new associate head coach. He previously guided his alma mater to WCAC titles in 2019 and 2023.
One of the biggest rematches on the schedule comes in the MIAA A, where the Cavaliers and Eagles meet again after last season’s state championship game. The Cavaliers won that one 30-22 to claim their fourth straight title.
The state’s biggest Prince George’s County game lands in September, and it comes with a new coach on the Jaguars’ sideline. Frederick Groves takes over for Dameon Powell as the Jaguars prepare for that showdown.
Frederick County also gets a heavyweight rematch, as the Lancers and Bears meet again after last season’s MPSSAA 3A state championship game. The Lancers rolled to a 56-17 win in that one.
DeMatha’s schedule includes a late-season test against the Falcons in October, and the Stags enter the year with an undefeated 2025 season and the WCAC Capital championship behind them. Bill McGregor is taking a leave of absence, so Bryce Bevill will serve as interim coach.
The Panthers close the regular season by hosting the Florida-based Ascenders in a matchup between two of the top high school football teams in the country.
And when it comes to Montgomery County, the biggest rivalry of them all closes the list. The Jaguars and Cougars will meet again in a rematch of last year’s second-round playoff game.
The Jaguars are also the last team to beat the Cougars, doing it in the 2023 playoffs. Could they do it again this October?
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