On Saturday, the Vineyarders will take on the Nantucket Whalers for the 37th time in this storied rivalry for the Island Cup.

The rivalry game between the Vineyard and Nantucket football teams ended in victory for the Vineyarders, who defeated the Whalers 21-7 in a rough, penalty-filled game. Junior running back Jacob Cardoza scored two touchdowns.

The Island Cup rivalry between Martha’s Vineyard and Nantucket includes blowout wins and hard-fought losses. On Saturday the Vineyarders made history by defeating Nantucket 14-0 on Whaler home turf at the Island Cup.

The coveted silver trophy is back on Martha's Vineyard, with the Vineyard football team defeating Nantucket 14-0 in the annual Island Cup Saturday. Sophomore Jacob Cardoza carried the day with two touchdowns.

For one day every year, the Island Cup trophy sits on the sidelines of a football field, where its home for the next year will be determined. For the other 364 days, the trophy sits in a case.

Martha's Vineyard needed a touchdown. Twenty-six seconds left on the clock. Archrival Nantucket up 26-21. First and goal, seven yards to reach the promised land of the Nantucket end zone. Vineyard quarterback Alec Tattersall walked toward the stands of Dan McCarthy Memorial Field, raising his arms over his head — get on your feet, Vineyard, on your feet. His teammates followed suit, arms lifted, encouraging, and the once-quiet crowd roared back to life.

In 1988, head football coach Donald Herman had just started coaching at Martha’s Vineyard Regional High School and was unfamiliar with the Island Cup, the annual rivalry football game between the Vineyard and Nantucket. The game was scheduled to be played on Nantucket that year, so he went over to “the other island” early with the junior varsity team, meeting up with the Nantucket coach.

Success doesn’t materialize out of the thin air, and in the case of this year’s varsity football team, now 6-4 as they head into the Island Cup, the groundwork was laid four years ago, when the current seniors took their first starts for the junior varsity squad.

“We’re building the foundation,” junior varsity head coach Mike Magaraci said in a Gazette interview. “And then junior and senior year, you build the house.”

In 1991, Jason O’Donnell was on Coach Donald Herman’s first state championship football team at the Martha’s Vineyard Regional High School.

On Monday, Mr. O’Donnell is out on the field with the four other varsity assistant coaches alongside Coach Herman, helping the team prepare for the Island Cup this weekend.

When Charles McGrath wrote about the annual Island Cup game between the Martha’s Vineyard and Nantucket football teams for the New Yorker in 1984, he likened it to a fierce sibling rivalry. What mainland team could hope to drum up a rivalry as poignant with either of the Island squads? For all that the Vineyarders can’t stand about the Whalers, they also know that the only football team in the entire country that could possibly understand what it means to be an Islander is that of their brother-in-isolation, Nantucket.