Postgame update, Oct. 24: Middletown beat Monroe-Woodbury 50–12 on Friday to reach 8–0 and end the Crusaders’ five-game run in the series. Read the final and the Friday wrap. The scouting and series history below were written before kickoff.
Middletown has beaten every opponent on its 2026 schedule. The next one has won the last five meetings between these programs in KOT845’s available results.
That is the history behind Friday’s 6 p.m. game against Monroe-Woodbury. The Middies enter 7–0 after beating Newburgh 33–22. The Crusaders are 1–6. This year’s records favor Middletown, but Monroe has been the team ending several of the Middies’ recent seasons.
Two title games, two Monroe wins
Monroe-Woodbury beat Middletown 34–10 in the 2024 Class AA championship game and 28–21 in the 2025 final. Last year’s seven-point margin is the most recent entry in the series. The Crusaders also won the 2025 regular-season meeting 49–13.
The other two wins in the current five-game run were closer: 24–20 in 2023 and 16–12 in the 2024 regular season. Three of those five meetings were decided by seven points or fewer. Middletown’s most recent win in the available series results came in the 2022 semifinals, 14–7.
Those results explain the interest in tonight’s matchup. Middletown has already added a Newburgh win to its unbeaten season. Beating Monroe would end another opponent’s recent hold on the series.
Monroe still has a playoff race to play
The Crusaders’ 1–6 overall record does not establish elimination. Monroe enters 1–2 in qualifying Class AA games. In the current KOT845 calculation, a win at Middletown would move that record to 2–2 without guaranteeing a place. A loss would leave Monroe 1–3 without automatically eliminating it.
Middletown has secured a playoff place in that calculation. Its remaining AA games still affect seeding. Kingston–Newburgh tonight and Valley Central–Pine Bush on Saturday are part of the same race.
What the archive tells us
KOT845 currently has 52 previous meetings indexed between Middletown and Monroe-Woodbury, with Monroe leading those results 40–11–1. The earliest indexed meeting is a 6–0 Monroe win in 1977. That is the available archive, not a claim that every meeting has been recovered.
The recent sequence is the useful part tonight: five Monroe wins since Middletown’s 2022 semifinal victory, including two championship games. The 2026 Middies have earned their unbeaten record. At 6 p.m., they get their chance to change the next line in that history.
Open the Monroe-Woodbury–Middletown Game Center for recent meetings, records and playoff scenarios. See every Friday kickoff.
Series figures reflect KOT845’s available records before October 23, 2026; earlier meetings may be missing. Playoff scenarios are KOT845 calculations, separate from an official Section IX bracket announcement.
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