Massapequa Football’s Journey to Ending the Nation’s Longest Win Streak

Massapequa football (NY) and its recent run has been nothing short of impressive.

The Chiefs are coming off a 2025 season where they compiled a 12-0 record and completed a Long Island Class I three-peat.

The Build-up to the Big Game

With their sights set on a fourth straight title, the Chiefs had one particular game circled on their 2026 schedule as the season started to take shape.

That game was against Garden City – a Trojans’ squad in 2025 that went 12-0, captured their fifth Long Island Class II crown in a row and had a 66-game win streak that, at the time, was a New York State record.

Garden City was off to a 2-0 start in the 2026 season, which bumped its streak to 68 and now sat as the nation’s best.

The Chiefs were originally scheduled to host the Trojans on Saturday, but a game of this magnitude was moved to Hofstra University’s James M. Shuart Stadium.

While the contest was set, Mother Nature had other plans on the date. A Nor’easter filled with heavy rain and hurricane-force winds forced the game to be moved to Monday, Sept. 28.

Massapequa Dethrones Garden City in Front of Large Crowd

As predicted, the game didn’t disappoint. It was capped with a 21-14 victory for Massapequa, thanks to a late 29-yard touchdown reception by Dylan Milio, in front of 6,000 fans at Shuart Stadium.

New York High School Football -- Massapequa Chiefs — Dylan Milio (17) had a 29-yard, game-winning touchdown reception with 30 seconds left in Massapequa's 21-14 victory over Garden City on Monday. | Alex Ornstein

In the heat of the moment, the Chiefs became the NYS’s newest holder of the longest active high school football win streak at 26 games. At the same time, Garden City’s streak that lasted more than five years came to an end.

“It was amazing,” Milio said via Newsday. “Catching that ball, running into the end zone, turning around and just seeing the entire sideline and all the fans going wild. It was unbelievable.”

How it Happened

The score was only 7-0 Massapequa in the first half, courtesy of a 1-yard TD run by Luke Garguilo. In the second half, Garden City tied it at 7-7 when Brayden Robertiello cut to his right and dashed 60 yards for the score.

The Chiefs regained their lead at 14-7 after Justin Farrell ran eight yards for the TD. The Trojans, however, recorded the equalizer on a 5-yard rushing score by Robertiello to knot it at 14 apiece.

The buildup to Massapequa’s game-winning drive started with an interception by Ryan Chabus late in the second half. Chabus leaped in front of the pass, secured the pick and returned it 20 yards.

“We haven’t really seen that play much on film and we didn’t see it in practice that much,” Chabus said via Newsday. “I just knew that with two minutes left, they were looking to make a big play. I saw their quarterback backing up, so that told me it was a screen. The ball was in the air for a while, so I just went and got it.”

A few plays later, Massapequa faced a 3rd-and-21 from the Trojans’ 29-yard line with 36 seconds left on the clock. Garguilo then connected with Milio, who caught the pass at the 14-yard line then proceeded to dart into the end zone untouched with 30 seconds to go.

The Chiefs’ defense got the job done on Garden City’s final possession when they forced three consecutive incompletions.

“I told them that this is something you’re going to remember for the rest of your life,” Massapequa head coach Kevin Shippos said via Newsday. “It was a classic back-and-forth against the best of the best. We just had one more play than they did.”

Garden City Still in Pursuit of 6th Straight Title

After it went 68 games with losing since a defeat to Lindenhurst in the Class I Long Island Championship game on Nov. 30, 2019, Garden City is not giving up hope on a six consecutive title.

“We played a four-quarter war with a really physical (Massapequa) team,” Garden City coach Dave Ettinger said via Newsday. “They built it into a really big atmosphere, but it’s Week 3 and all of our goals are still ahead of us this year. Our guys should have nothing to be ashamed about.”

As for the Chiefs, they completed a game that will go down in history in front of a large crowd.

“It’s a Monday evening and look at this crowd,” Shippos said via Newsday. “It’s great for people to see these championship programs. The game could have gone either way and we were fortunate it went our way. High school sports are about putting your kids at the highest level of competition. We both learn from this and it’s a shame one streak must end but it’s not about that. It’s about setting these kids up to be successful in life, and too many people get lost in the stuff that doesn’t matter. What matters is getting them to be good young men.”

Who Does the Nation’s Longest Win Streak Belong to Now?

The high school football team with the nation’s longest win streak now belongs to Carl Albert in Midwest City, Oklahoma. The Titans have currently won 58 games in a row and have not lost since Sept. 9, 2022.

Sheridan High School (WY) previously had the second-longest win streak at 59 games when Garden City was at the top, but the Broncs’ run ended following a 38-0 loss to Natrona County over the weekend.

What’s next for Massapequa, Garden City

The Chiefs (3-0) will go up against Hempstead on Friday at 6 p.m. The Trojans (2-1) will host New Hyde Park Memorial on Saturday at 3 p.m.

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