Coach I Picks Week 5: All 20 Games, With Three Tough Calls

Final results: 18–2 in Week 5. Coach I went 2–0 Thursday, 12–1 Friday and 4–1 Saturday. New Paltz and Pawling won; Marlboro beat the Highland pick. Ellenville’s Friday win was the other miss.

The running season ledger is 95–28 overall and 85–19 in matchups between Section IX teams. All 20 games are final. Eldred and Burke Catholic won the last two picks, completing the Week 5 ledger.

Every Friday final → · Saturday kickoff guide →

Read Coach I’s take on every Week 5 result →

Original picks and reasoning

Week 5 • October 8–10, 2026

Coach I comes into Week 5 off a 19–2 week. The season ledger is 77–26, including 67–17 in matchups between Section IX teams, as recorded in our Week 4 results recap.

Twenty games. Two Thursday openers. Thirteen Friday matchups. Five Saturday finishes. These are winner picks, with every matchup linked to its Game Center. Kickoff times are Eastern and reflect the current KOT845 schedule.

Read the new Power 40 and the reasoning behind every spot · Open Game Night · Full schedule

Thursday, October 8

Saugerties at Beacon

6:00 p.m. • Pick: Beacon

I’m going with Beacon. I think the Bulldogs are the better team, and they have more offense. The concern is the defense. If Beacon plays the way it did in the first half against New Paltz, this could become more of a game than expected. Beacon led 40–34 at halftime last Friday before shutting New Paltz out in the second half. That second-half defense is what needs to carry over.

Game Center: Saugerties at Beacon →

Tri-Valley at Pine Plains/Rhinebeck

7:00 p.m. • Pick: Tri-Valley

I’m going with Tri-Valley. Pine Plains/Rhinebeck has struggled lately, and Tri-Valley has put together a strong start. The Bears are 3–1, with an 18–16 win over Onteora and consecutive wins over Fallsburg and Rockland. Pine Plains/Rhinebeck has lost its last two games. I like Tri-Valley to keep building.

Game Center: Tri-Valley at Pine Plains/Rhinebeck →

Friday, October 9

Kingston at Monroe-Woodbury

6:00 p.m. • Pick: Monroe-Woodbury

For the picks ledger, I’m going with Monroe-Woodbury. But Kingston has a real opportunity here. Monroe is 0–5 and has not produced much offense recently: seven against Cornwall, six against Minisink and seven against Newburgh. Its season high was 20 in the opener against John F. Kennedy Campus, followed by 14 against Washingtonville.

This game comes down to two questions: Can Kingston score on Monroe’s defense, and can the Tigers hold this struggling Monroe offense down long enough for their own offense to find a touchdown? Neither offense has given us much reason to expect a shootout.

I would like Kingston more at home. Another Monroe loss would be jaw-dropping, and a stark measure of how far the Crusaders have fallen since last year’s Class AA championship. It should be a very tough game.

Game Center: Kingston at Monroe-Woodbury →

Valley Central at Middletown

6:00 p.m. • Pick: Middletown

I’m going with Middletown, and I’m going with its defense. Valley Central has earned respect with its 4–1 start, but the unbeaten Middies’ defense is the difference I’m backing in this matchup.

Game Center: Valley Central at Middletown →

Newburgh Free Academy at Pine Bush

6:00 p.m. • Pick: Newburgh Free Academy

I’m going with Newburgh. The Goldbacks have looked scary against Section IX opponents. Pine Bush put together a solid first half against Middletown in the Battle of 211, going into halftime tied 7–7. Recent meetings with Newburgh have been much less encouraging, including last year’s 56–6 loss. Let’s see if Pine Bush can change that, or if Newburgh makes one more statement before heading to current No. 1 Middletown next week.

Game Center: Newburgh Free Academy at Pine Bush →

Goshen at FDR

6:00 p.m. • Pick: Goshen

I’m going with Goshen. FDR has lost three straight after opening 2–0, and the Presidents have not shown they are ready to compete with this tier of Class A opponents. Goshen needs a response after the Washingtonville loss, and I’m rolling with the Gladiators here.

Game Center: Goshen at FDR →

Monticello at Poughkeepsie

6:00 p.m. • Pick: Monticello

I’m rolling with Monticello. The Panthers are in a bit better shape after getting their first win. Their defense came up with three interceptions against Liberty, and Liberty hurt itself with mistakes. Can Poughkeepsie play a cleaner game, score its first touchdown of the season and do what Monticello did last week—turn an opportunity into its first win? This is a big chance for the Pioneers. If it slips away, Poughkeepsie, like Liberty, remains in danger of going winless in 2026.

Game Center: Monticello at Poughkeepsie →

Wallkill at Washingtonville

6:00 p.m. • Pick: Washingtonville

I’m going with Washingtonville. Like FDR, Wallkill still has to prove it can play with this tier of Class A opponents. The Wizards just put up 37 against Goshen. Even if Wallkill can score, does it have the defense to slow Washingtonville down for four quarters? That is the question, and I’m backing the Wizards.

Game Center: Wallkill at Washingtonville →

Red Hook at Port Jervis

6:00 p.m. • Pick: Port Jervis

I’m going with Port Jervis. Red Hook just scored 20 against Marlboro and played a great game. The Raiders will want to carry that performance into this matchup. Port is coming off a 33–0 win over Saugerties, and I’m backing Port to get another win. Red Hook has something to build on, but this is another tough test.

Game Center: Red Hook at Port Jervis →

James I. O’Neill at Spackenkill

6:00 p.m. • Pick: James I. O’Neill

I’m going with O’Neill. Spackenkill has played two great games over the last two weeks, but both ended in the loss column against Rondout and Chester. O’Neill is coming off a 23–8 win over Rondout in its first game back after two weeks without a played game. I’m taking the Raiders on the road, but this may be tighter than it seems.

Game Center: James I. O’Neill at Spackenkill →

Sullivan West at Fallsburg

6:00 p.m. • Pick: Sullivan West

I’m going with Sullivan West. Fallsburg is still struggling to find its first win, while Sullivan West has been playing well. The Bulldogs have the stronger body of work, and I’m backing them to keep it going.

Game Center: Sullivan West at Fallsburg →

Warwick at Cornwall

7:00 p.m. • Pick: Cornwall

I’m going with Cornwall. This is a rematch of the 2025 Class A semifinal, which Cornwall won 50–6. The Dragons also beat Warwick 48–14 in the 2024 semifinal. Warwick has not won a game this season, and I’m expecting Cornwall to take care of this matchup again.

Game Center: Warwick at Cornwall →

Minisink Valley at Our Lady of Lourdes

7:00 p.m. • Pick: Our Lady of Lourdes

I’m going with Lourdes because of its scoring ability. Minisink is a tough team, and it is not going to shy away from this matchup. Last season, Minisink beat Lourdes twice on its way to the sectional championship game. The Warriors know the recipe. Can this team use the same formula and pull out another win? Absolutely. But I’m picking Lourdes to win this one. Lourdes does need to tighten up its defense at this point in the season.

Game Center: Minisink Valley at Our Lady of Lourdes →

Rondout Valley at Dover

7:00 p.m. • Pick: Dover

I’m going with Dover. You have to imagine the Dragons are frustrated after last week’s loss to Highland. Now the focus is on what they can do to reach the Class C championship and earn another shot at Highland if that is who they meet there. I expect Dover to come in refocused, and I’m backing the Dragons to respond against Rondout.

Game Center: Rondout Valley at Dover →

Millbrook at Ellenville

7:00 p.m. • Pick: Millbrook

I’m going with Millbrook. The Blazers have put together a strong season, and I’m sticking with them here. These eight-man games can turn into high-scoring matchups, and Ellenville has a player who can make this one interesting: this week’s KOT845/MHVFCU Student-Athlete Spotlight, James Horvath. The do-it-all quarterback will do everything in his power to make this pick go the other way. Horvath gives the Blue Devils a reason to believe, but Millbrook is the pick.

Game Center: Millbrook at Ellenville →

Saturday, October 10

New Paltz at Liberty

1:00 p.m. • Pick: New Paltz

I’m going with New Paltz. The Huguenots are a much better 0–5 team than their record makes them look. They have shown they can compete, and I’m backing them to get their first win against Liberty.

Game Center: New Paltz at Liberty →

Highland at Marlboro

1:00 p.m. • Pick: Highland

Every week, I like to take one pick that goes against the rankings or what people expect. We called Newburgh over Cornwall earlier this season. Now I’m calling Highland to beat Marlboro in the Black and Blue Bowl for its first win in the rivalry since 2009.

This could make me look foolish. Highland lost 52–6 to Class D Burke Catholic on September 25 before responding with a win over Dover last week. But I do not believe Marlboro’s offense is as explosive as Burke’s, or that the Dukes will find an easy 52 points while holding Highland to six. If the Huskies need a little extra juice to end this drought, here it is: Coach I is picking Highland.

What could make this pick wrong? Marlboro’s defense. The Dukes are stingy. They may bend, but they are difficult to break, and beating Marlboro is never easy. Highland will have to earn its points. I’m taking the chance and hoping the Huskies prove me right.

Game Center: Highland at Marlboro →

Eldred at Rockland Central

7:00 p.m. • Pick: Eldred

I’m rolling with Eldred. This is the defending champion against a struggling Rockland team. It would be a major surprise for Rockland to put together a win here, and I’m backing the Yellowjackets.

Game Center: Eldred at Rockland Central →

Pawling at Onteora

1:00 p.m. • Pick: Pawling

I’m rolling with unbeaten Pawling. I expect the Tigers to run the table; right now, they look a step ahead of everyone else in eight-man. It is still high school football. Things can surprise you and shock you. But I’m going with what we know right now, and Pawling is the pick.

Game Center: Pawling at Onteora →

John S. Burke Catholic at Chester Academy

7:00 p.m. • Pick: John S. Burke Catholic

I’m going with Burke Catholic on Saturday night at Chester Commons Park. For the first few weeks, I kept Chester at the top of Class D until Burke proved it. Burke has proved it. I never ranked the Eagles behind Chester because I thought they were the worse team; I thought Chester had earned that spot. At this point in the season, the evidence has changed.

I believe Burke could run away with this game. If that happens against the defending Class C champion, it would be a strong sign that the Eagles could take control of the Class D championship race, too. Burke has had a long grip on this class. Chester gives it a real challenger, and Saturday is the chance to show how much separation remains. I think Burke is very good, and I’m backing the Eagles to win.

Game Center: John S. Burke Catholic at Chester Academy →

The closest calls

Kingston–Monroe, Minisink–Lourdes and Highland–Marlboro are the games I would circle for debate. The picks are Monroe-Woodbury, Lourdes and Highland, but each opponent has a clear path to changing the conversation.

Follow the Game Night board for posted score updates and return to each Game Center for results and matchup coverage.