25 Can't-Miss Maryland High School Football Games in 2026

Championship rematches. Historic rivalries. Interstate showdowns.

Maryland's 2026 high school football schedule is loaded with games that could shape conference races, playoff brackets and statewide rankings long before November arrives. From Week 1 blockbusters to late-season rivalry clashes, here are the 25 regular-season matchups we're most excited to watch this fall.

If you're only able to make a few games this season, these should be at the top of your list.

No. 25-16: Great Early-Season Tests

25. Bethesda-Chevy Chase at Churchill, Friday, Sept. 4

Since 2021, head coach Joe Rydzewski has turned the Bulldogs into contenders. Meanwhile, Matt Schwartzback has made the Barons one of the more intriguing teams in Montgomery County the past few years. This season opener should set the tone for how both teams will play in 2026.

24. Quince Orchard at Stone Bridge (VA), Friday, Sept. 18

John Kelley's Cougars continue their yearly tradition of facing the Virginia-based Bulldogs. Quince Orchard will head to Ashburn for the annual matchup, coming off a tight 20-0 win in Gaithersburg last year.

23. Saint Frances Academy at DeLand (FL), Friday, Aug. 28

Messay Hailemariam's Panthers were the top-ranked team in High School On SI's Maryland Football Power 25 rankings in 2025, finishing 9-1. They open the 2026 season against the Florida-based Bulldogs, who went 13-1 last season.

22. Gilman at Bullis, Friday, Sept. 4

The Bulldogs finished 2025 with a share of the Interstate Athletic Conference (IAC) title. One of their earlier matchups in the season is against the Baltimore-based Greyhounds, who have won 13 MIAA championships since 1998.

21. Dunbar at Milford Mill Academy, Friday, Sept. 4

The Poets are coming off winning the 2025 MPSSAA 2A/1A state title. The Millers made it to the 3A semifinals. This Baltimore City vs. County matchup will open the 2026 season at Under Armour Stadium.

20. Mergenthaler Vo-Tech at Linganore, Saturday, Sept. 5

Both schools won MPSSAA state championships last season, with the Mustangs claiming the 4A/3A title, and the Lancers taking the 3A title.

19. Georgetown Prep at St. Mary's, Saturday, Aug. 29

Dan Paro's Little Hoyas head up to Annapolis to open the season, as the Saints will be led by rising senior quarterback DJ Hitaffer.

18. Paint Branch at Quince Orchard, Friday, Sept. 4

The annual opening matchup between the Panthers and Cougars is always one to keep an eye on. John Kelley's squad heads into the contest with 27 consecutive wins and back-to-back MPSSAA 4A state championships.

17. Archbishop Spalding at St. John's (DC), Friday, Sept. 4

The Cavaliers enter the 2026 season without longtime head coach Kyle Schmidt, as Robert "R.B" Green has taken over. They begin the month of September against the Cadets in their second of three WCAC matchups to begin the year.

16. Archbishop Spalding at Good Counsel, Friday, Sept. 11

The following week, the Cavaliers head to Olney to face the Falcons, their third and final WCAC opponent to open 2026.

Games 15-6: Playoff-Caliber Matchups

15. Severna Park at Broadneck, Friday, Oct. 30

The Bruins have won the last 15 meetings against the rival Falcons. The Annapolis-based school could possibly make it 16 on Halloween weekend. Head coach Rob Harris led Broadneck to the MPSSAA 4A state semifinals in 2025.

14. Wise at Eleanor Roosevelt, Saturday, Oct. 10

Steve Rapp's Pumas are coming off back-to-back appearances in the MPSSAA 4A state title game. The Raiders are coming off a solid 7-3 2025 season. This Prince George's County matchup should be interesting.

13. McDonogh at Gilman, Sat. Nov. 7

With Gilman back in the mix as a MIAA playoff team last year, the 100th renewal of one of the nation's most eduring private school football rivalries takes on renewed significance. The Eagles have dominated recently, but Gilman still leads the all-time series, 61-41.

12. Landon at Bullis, Friday, Oct. 16

The Bulldogs may not have Georgetown Prep on their regular season schedule, but their October home matchup against the Falcons is still a matchup to keep eyes on.

11. Gonzaga (DC) at Good Counsel, Friday, Oct. 23

The Falcons enter the 2026 season under a new head coach, as Sal Gorgone takes over for Andy Stefanelli. Their late-October matchup against the WCAC rival Eagles should still be a good one.

10. Churchill at Quince Orchard, Friday, Oct. 2

Two of the best teams in Montgomery County meet again in October, though John Kelley's Cougars have owned Joe Rydzewski's Bulldogs in all four meetings.

9. St. Mary's Ryken at Paul VI (VA), Friday, Oct. 9

It's a rematch of last season's WCAC Metro title game, with the defending champion Knights looking to keep the momentum going as they visit the Panthers in Chantilly.

8. St. John's (DC) at Good Counsel, Friday, Oct. 16

Andy Stefanelli makes his return to Good Counsel as the Cadets' new associate head coach. Stefanelli had previously led his alma mater to a pair of WCAC titles in 2019 and 2023.

7. McDonogh at Archbishop Spalding, Friday, Oct. 9

It's a rematch of the 2025 MIAA A state championship game, where the Cavaliers beat the Eagles 30-22 to claim their fourth straight title.

6. Wise at C.H. Flowers, Friday, Sept. 18

The biggest matchup in Prince George's County will take place in September. The Jaguars enter the upcoming season under new head coach Frederick Groves, taking over for Dameon Powell.

Top Five: Maryland's Must-See Matchups

5. Oakdale at Linganore, Friday, Oct. 19

The two rival Frederick County schools face off in a rematch of last season's MPSSAA 3A state championship game, where the Lancers crushed the Bears 56-17.

4. Good Counsel at DeMatha, Friday, Oct. 9

The Stags are coming off an undefeated 2025 season and the WCAC Capital championship. However, with legendary head coach Bill McGregor taking a leave of absence, it's up to interim coach Bryce Bevill to lead the way. DeMatha will face the rival Falcons under their new head coach in October.

3. IMG Academy (FL) at St. Frances Academy, Friday, Nov. 13

The Panthers finish the regular season by hosting the Florida-based Ascenders in a battle between two of the top high school football teams in the country.

2. DeMatha at Archbishop Spalding, Friday, Aug. 28

Two of the top teams in the state, the Stags and Cavaliers will face off under new head coaches to open the season. Both teams are also coming off respective championships.

1. Quince Orchard at Northwest, Friday, Oct. 23

We finish with the biggest rivalry in Montgomery County and a rematch of last year's second-round playoff meeting. The Jaguars are also the last team to have beaten the Cougars, having done so in the 2023 playoffs. Could they do it again this October?

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