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Friday, November 13, 2026Local news for Redington Beach and Florida.
Redington Beach Herald · 13575 58th Street North, Suite 200, Clearwater, FL 33760
Sports · Sioux Falls

Freeman Flyers Face Castlewood in Bid for First Solo State Title Since 1999

The undefeated team plays Friday night at 7 p.m. for a chance to return to the state championship game after a twelve-year hiatus from varsity competition.

By Nadia Rahman ·

Illustration for: Freeman Flyers Face Castlewood in Bid for First Solo State Title Since 1999
Illustration generated for this article, not a news photograph.

Freeman high school football players will play at 7 p.m. on Friday night for a spot in the state championship game. The Flyers, who have not won a title as an independent program since 1999, host Castlewood in the Class 9A semifinals. A win would secure the team's first appearance in a state final since the end of their historical dynasty.

The program's current status follows a twelve-year absence from varsity competition. In 2015, the team vacated its season after fielding only ten players. This marked the end of an era that began in 1981, when the Flyers won one of the first state titles under the new playoff system. Under coach Jim Eisenbrey, the team became a dominant force, winning four consecutive championships from 1997 to 2000.

After Eisenbrey retired in 2004, the team experienced a gradual decline. From 2012 to 2014, the Flyers went winless in three consecutive seasons. Participation numbers dropped sharply, leading to the decision to stop playing varsity football in 2015. For the next ten years, Freeman students played in cooperative leagues with Canistota and Marion, winning four state titles with Canistota and a 9AA title with Marion last year.

The Flyers returned to independent status for the 2026 season after Marion formed an all-sports partnership with Parker. Freeman officials determined that local enrollment was sufficient to support a standalone team. The new squad began its season on August 21, 2026, with a game against Alcester-Hudson. Since then, the team has maintained the number one ranking in Class 9A.

The current roster holds a 10-0 record. Their next opponent, Castlewood, is also undefeated. The game will be played at the Freeman stadium. This contest represents the first time in twelve years that the Freeman Flyers have competed for a state championship berth as a solo program.

The team's last victory in a state title game came in 1999. In that championship match, the Flyers defeated Harding County with a score of 12-8. That win was the fourth of four consecutive state titles for the program.

Freeman residents and former players have discussed the sustainability of the new program amid declining rural population trends. The team's current success has drawn attention to the effort required to maintain a competitive roster in a small community.

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