Game day: Friday, October 16, 2026 • 6 p.m. • Faller Field, Middletown
Middletown’s last four on-field wins over Newburgh all came at Academy Field.
The breakthrough in spring 2021. Both meetings in 2023, including the sectional championship. Last November’s semifinal upset. Every one of those moments happened on Newburgh’s turf.
Tonight, the Middies get another chance to bring that success home.
Middletown enters Faller Field 6–0. Newburgh Free Academy arrives 5–1, riding five straight wins. Both are 2–0 in Class AA. The 6 p.m. kickoff brings together two contenders whose rivalry has become much harder to predict.
Before Newburgh’s run, Middletown had its own
This matchup reaches well beyond the modern scoreboard archive. A Port Jervis yearbook’s account of the 1905 season records a Middletown victory over Newburgh. Both schools later became founding members of the DUSO football league in 1923.
Generations of players have inherited the matchup. They have inherited very different versions of it.
In KOT845’s available modern score ledger, Middletown won 11 straight played meetings from 1987 through 1996. The 1994 team supplied the clearest statement: Dick Wolslayer’s Middies beat NFA 32–0 in the regular season and 27–0 in the Section IX Class A final, played at Dietz Stadium in Kingston.
Middletown followed with wins in 1995 and 1996. Then Newburgh won 40–12 in 1997, beginning a stretch of 22 consecutive played victories through 2019 in that ledger. NFA also received a separate forfeit win in 2013.
For more than two decades, the Goldbacks kept the result on their side. Middletown had to change that before it could change the conversation.
The breakthrough became a real rivalry again
On April 9, 2021, Middletown finally did it. The Middies won 22–14 at Newburgh during the pandemic-delayed spring season.
Newburgh answered by winning the fall rematch. In 2022, the Goldbacks shut Middletown out twice, including 35–0 for the Class AA championship.
Then Middletown answered back. The Middies won the 2023 regular-season meeting 28–17 and returned for a 26–14 championship victory. Both were played at Academy Field. Even though Middletown was the designated home team for the final, the championship venue was Newburgh.
The latest reversal came last season. NFA beat Middletown 35–0 in September. When the teams met again in November, Middletown won 21–16 at Academy Field and ended the Goldbacks’ season.
Newburgh’s players carried that semifinal loss into their offseason. In KOT845’s preseason interview, Austin Lilla described “a different mindset going into this year.”
The recent results reflect the change. NFA leads the nine played meetings since spring 2021 by just 5–4. Middletown has won three of the last five. The Middies’ four victories in that stretch all happened at Academy Field, giving tonight’s return to Faller a significance the records alone cannot capture.
What this year’s teams bring to Faller
Middletown has allowed 48 points in six games, an average of eight. The Middies shut out Arlington and Minisink Valley and held Port Jervis and Valley Central to seven apiece. Their closest call was a 22–21 road win over Cornwall.
Newburgh has been overwhelming since its opening loss to Curtis. The Goldbacks have outscored their next five opponents 207–38, winning every game by at least 31 points. That run includes a 31–0 win over Cornwall and a 38–7 win over Monroe-Woodbury. Those totals come from the 2026 Section Nine scoreboard.
That puts a direct question in front of both teams: can Middletown slow Newburgh’s scoring pace, and can the Middies generate enough offense against a Goldbacks team that has allowed no more than 13 points in any of its five wins?
Last year’s two meetings are a useful warning against treating one result as a permanent verdict. Friday gives the winner a third league victory and a stronger position in the Class AA race. November will still require its own answers.
History at the gate
The date carries another Middletown connection. October 16 was Wolslayer’s birthday. In 2024, the district named the entrance to the Faller Field Stadium Complex “Wolslayer Gate” in his memory.
The coach whose Middies shut out Newburgh for the 1994 sectional title is part of the setting tonight. Inside, the current Middies have an unbeaten season to protect. Newburgh has a five-game surge to extend and a semifinal loss to answer.
At 6 p.m., the rivalry returns to Faller.
Historical note: The streaks above describe located modern results, not a complete all-time series. Played-game totals exclude NFA’s 2013 forfeit award and Middletown’s 2024 semifinal advancement by forfeit.
Follow the matchup: Newburgh–Middletown Game Center · The statistical preview and playoff scenarios · Middletown program page
Join the Conversation
Keep it respectful and focused on the story. First-time comments may be held for moderation.