Monticello–Poughkeepsie Isn’t About the Top of the Standings. That’s Why It Matters So Much.

Monticello brings its first win into Poughkeepsie Friday. For two rebuilding programs, this is the kind of game that can move the needle—and give one group of kids something real to build on.

Friday result: Monticello 22, Poughkeepsie 8. Monticello has two straight wins and is 2–4. Poughkeepsie is 0–6. Monticello visits Saugerties Thursday, October 15, at 3:30 p.m.; Poughkeepsie hosts Spackenkill Friday at 7 p.m.

Read the Monticello follow-up →


Original pregame analysis

Monticello at Poughkeepsie is not a game between two teams fighting for the top of the Section IX rankings.

That does not make it small.

For these two programs, Friday night might be one of the most important games on the Week 5 schedule.

Monticello (1-4) visits Poughkeepsie (0-5) at 6 p.m. Friday with both programs still trying to build their way toward something more sustainable. One of them gets to leave Friday with a win. For teams that have spent too many recent seasons on the wrong side of the scoreboard, that matters.

Open the Monticello at Poughkeepsie Game Center →

Monticello finally got the breakthrough

Last Thursday changed the feel of Monticello’s season.

The Panthers went to Liberty 0-4 and left with a 24-22 win.

It was not perfect. Liberty returned the opening kickoff for a touchdown. Monticello lost a fumble before halftime. The RedHawks kept coming and eventually pulled within two.

But Monticello made winning plays.

The Panthers took the ball away from Liberty three times. One takeaway gave Monticello the ball deep in Liberty territory and helped set up Dion Knight for a short-yardage touchdown. Another interception near the goal line stopped Liberty from taking the lead before halftime.

Then the Panthers created explosive offense.

Kavon Cox scored on runs of 86 and 77 yards. Quarterback Tahir Atkins added a 76-yard touchdown late in the third quarter. Monticello made enough plays on both sides of the ball to finally finish one.

Read: Monticello Breaks Through, Holds Off Liberty 24-22 →

One win can matter more when winning has been hard

That is what makes Friday so interesting.

Monticello does not have to imagine what a few wins can do for a struggling program. The Panthers experienced it two years ago.

In 2024, Monticello won three games: Liberty, James I. O’Neill and Chester.

The Chester win was especially significant. Monticello beat the Hambletonians 16-8. Chester recovered from that loss, reached the Section IX Class C championship game and beat Dover 43-12 for the title.

So a Monticello team that struggled through much of that season still got to walk away knowing it had beaten the eventual sectional champion.

KOT845’s current archive review has not identified an earlier Monticello win over a team that went on to capture a Section IX championship that same season. At minimum, it is one of the most significant wins in the program’s available modern history.

Three wins in 2024 meant something

Monticello’s documented modern high is five wins. The Panthers won four games in 2016.

That makes the three-win 2024 season important in context: it was Monticello’s highest win total since 2016 and one of the better seasons in the program’s available modern record.

Three wins will not hang a championship banner.

For a program trying to establish belief, participation, continuity and a reason for kids to keep coming back, three wins can still change the experience of a season.

Those players got to beat O’Neill. They got to beat Liberty. They got to beat a Chester team that eventually became a champion.

They got to experience what finishing a Friday night on top feels like.

That is a ceiling the current group can see.

So what is the goal now?

Monticello is 1-4.

The Panthers are not suddenly fixed because they beat Liberty. One win does not erase the issues that have followed the program for years.

But now there is something tangible to chase.

Can Monticello turn one win into two?

Can it get back toward the three-win mark from 2024?

Can this group give younger players another reason to believe that showing up, staying together and continuing to work can eventually produce a result?

Those are meaningful goals for where this program is right now.

Poughkeepsie has not always been here either

It is important not to talk about Poughkeepsie as though losing is simply what the program has always done.

It is not.

The Pioneers went 9-1 in 2011 and 6-2 in 2012. Available results show a 4-3 season as recently as 2021.

The decline since then has been steep, and 2026 has continued it. Poughkeepsie enters Friday 0-5 and still searching for a breakthrough.

But there are players in that locker room who deserve an opportunity to experience the other side of a Friday night too.

That is why Monticello coming to Poughkeepsie matters.

Read our earlier deep dive: Beyond 0–263 — What It Will Take to Rebuild Poughkeepsie and Monticello Football →

Poughkeepsie has won the last two meetings

These programs have not met often in the available KOT845 archive.

There are three indexed meetings:

  • 2014: Monticello 34, Poughkeepsie 26
  • 2015: Poughkeepsie 24, Monticello 20
  • 2016: Poughkeepsie 40, Monticello 20

Poughkeepsie therefore leads the indexed series 2-1 and has won the last two meetings.

Ten years after that 2016 game, the programs meet again in a very different place.

Explore Monticello–Poughkeepsie history →

This is what rebuilding actually looks like

We wrote earlier this season about what it will take to rebuild these programs.

The answer was never going to be one coach, one speech, one offseason or one game.

It is participation. Retention. Coaching continuity. Assistant coaches. Modified football. Youth football. Weight-room attendance. Academics. Families. District support. Community involvement. Standards. Accountability.

And somewhere inside all of that, kids still need to experience winning.

That part cannot be ignored.

You can tell a teenager that the program is improving. You can tell him the weight room numbers are better. You can tell him the roster is growing. You can tell him the future is coming.

Eventually, he needs to see the scoreboard say it too.

For now, these games are enormous

Monticello, Liberty and Poughkeepsie are not currently beating the top programs in Section IX with any consistency.

That is the reality.

So when these programs play one another, the game carries a different kind of weight.

Liberty had a chance last week. Monticello took it, 24-22.

Now Poughkeepsie gets Monticello.

Later, there will be bigger goals. Competing for league titles. Reaching playoffs. Beating ranked teams. Building seasons where three wins no longer feel exceptional.

But programs do not jump from the bottom to those goals in one move.

They move the needle.

One competitive quarter. One takeaway. One touchdown. One close game. One win. Then another.

Friday gives Monticello and Poughkeepsie a chance to move it again.

Game information

  • Matchup: Monticello at Poughkeepsie
  • Date: Friday, October 9, 2026
  • Kickoff: 6:00 p.m.
  • Site: Poughkeepsie High School
  • Monticello: 1-4
  • Poughkeepsie: 0-5
  • Indexed series: Poughkeepsie leads 2-1

Follow the full Week 5 slate and KOT845 Game Night throughout the weekend.

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Filed under: Football
About the Author

Isaac Cayetano

Founder & Editor-in-Chief, Kings of the 845

Isaac Cayetano is the Founder and Editor-in-Chief of Kings of the 845 (KOT845), covering Section IX football, basketball, rankings, community stories, and Hudson Valley sports culture. A football coach and longtime Section IX analyst, Isaac founded KOT845 in 2020 to create the Hudson Valley's premier sports and community media platform.

View All Articles by Isaac Cayetano →
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