The Can’t-Miss Long Island High School Football Rivalry Games of 2025

From the Parkway Power Bowl to overtime thrillers, these heated matchups will define the season for players, coaches, and entire communities

Bryce Ciancuelli of St Anthony's leading his team out of the tunnel. St Anthony's vs Chaminade is one of Long Island's greatest rivalries. / Savas Sioutopoulos/ Savas Media

Some high school rivalry games on Long Island just mean more. When certain schools face off, it’s more than just football. Student bodies, alumni, and entire communities come together to watch their team go to war against their arch rival.

Classic Rivalries You Can't Miss

Longwood at William Floyd - Oct. 4

Two powerhouses in Suffolk County Division 1 have been going to battle for a very long time. The Parkway Power Bowl is a special event for two communities that love high school football.

Longwood brings back one of the best defensive players on Long Island in Kaden Reid. The Lions are always tough in the trenches, with Michael Durate leading a solid group as they prepare to battle the "Mastic Beach Monsters."

William Floyd’s Matthew Benjiman, Jeru Hall, and Joe Melecio lead the lineman unit, and they’ll be blocking for All-State RB Ja’Quan Thomas..

St. Anthony's at Chaminade - Oct. 18

One of the reasons athletes go to these schools is to play in this game. St. Anthony’s vs. Chaminade is one of the biggest stages in any sport on Long Island.

Last season, Chaminade took down St. Anthony’s in the fall for the first time since 2012. The Flyers return some great, experienced leaders, including Declan Miller, Luca Smith, Brady Murray, Michael Genovese, and Anthony Trapani.

St. Anthony’s brings back two of the most electric players in the state. ATH Kevin Moore (Delaware commit) and four-star running back Xavier Bala make the Friars must-see TV for everyone on Long Island. Key seniors like Bryce Ciancuelli, Johnny Russo, and DJ Garcia will be crucial for St. Anthony’s this season.

Sachem East at Sachem North - Oct. 18

The Sachem community loves football, and when these two teams meet, it’s always a battle. Sachem North won the last meeting and returns several key players.

Quarterback Luke LaRocca had a strong sophomore season and forms a solid duo with speedy receiver Henry Sarro. Up front, James Chirchella and the Sachem North offensive line recently took home the National Football Foundation Lineman Challenge trophy.

They will face a talented Sachem East line. Jack Martines, a Princeton commit, is one of the best offensive linemen in the state. Frankie Colon is also a standout two-way lineman for East. On defense, Ryan Lanes and Brayden King will be key contributors.

Farmingdale vs Massapequa - Oct. 18

A special tradition between these two towns, this game gets circled every single year, and this season is bound to be special. Massapequa beat Farmingdale in a dramatic overtime win for the county title last season, and both teams return serious star power.

The Chiefs bring back two of their top skill players in Andrew Pedalinio and Cole Villalta. A solid number of linemen return as well, featuring Tristan Tarasi.

For Farmingdale, Jordan Petzold and Jack McCarthy lead a strong lineman group, and they’ll be blocking for their stars Josh Kama and Michael Galgano. On defense, Mateo Morales is one of the best edge rushers on Long Island.

Rivalry Games On The Rise

Half Hollow Hills East At Bellport - Oct. 11

Ever since these two teams met in the 2021 playoffs these meetings have felt more personal. In the fall of 2021, Bellport won a chaotic semi-final game over Half Hollow Hills East. They have met in the playoffs three of the last four years, and every game has been extremely physical between these two teams.

Hills East is the favorite in Division 2. They bring back All-State running back Daniel White, running behind a massive offensive line led by Trevon Cole-Jenkins and Keith McDowell.

Braydon Cipp leads a Bellport offense looking to make noise this season. On defense, Elie Malcom and Davide Lopes are two hard hitters featured in a fearless Clippers defense.

Westhampton Beach at Sayville - Oct. 18

Two more outstanding football towns on Long Island, Sayville and Westhampton have had some amazing matchups in recent memory, featuring all-time greats like Jack Coan and Dylan Laube. This year promises to be a very fun game between these squads in a playoff rematch.

Defending champion Sayville brings back quarterback Patrick Coan (Lehigh commit) and wide receiver Luke Neugebauer. Keith Kolar leads an always tough Golden Flashes defense.

For the Hurricanes, they return a rising star in Jake Calloway, who will be running behind a massive offensive line led by Ben Magee and JP Peters. Patrick Fay and Andrew Lewis are also x-factors for Westhampton.

Seaford at Plainedge - Oct. 31

After last season’s instant classic, this matchup is one everyone is looking forward to. Jaxson Torres’ last-second Hail Mary gave Plainedge a dramatic win over Seaford to advance to the county championship.

Now in Plainedge’s second year in Conference IV, it’s the first time in what seems like forever they won’t be playing Bethpage or Wantagh. But neighboring school Seaford is a great fit as their next rival — especially considering what happened last season.

Both communities will be amped for this regular-season finale. Each team returns an elite QB-RB duo: Seaford features Michael Spinella and Brian Falk, while Plainedge brings back Jaxson Torres and Dylan Fella.