The Island Cup is always a day to circle on the calendar. But this year, it’s an event to circle with a bigger, bolder marker.

Eagles owner and Edgartown seasonal resident Jeffrey Lurie is likely the only NFL owner with multiple Academy Awards and a doctorate in social policy.

Martha’s Vineyard Regional High School new football coach Tony Mottola doesn’t bark at his players during practice.

The Martha’s Vineyard Regional High School has found a new head football coach in Tony Mottola, a former member of the Las Vegas Raiders coaching staff.

On Sunday evening, at the season-end football banquet, Don Herman announced his retirement after 32 years coaching football at the regional high school. It was the second time for the longtime coach to retire.

A 7-6 lead took the Vineyarders into the second half against Dennis-Yarmouth Saturday. But at halftime, the game became about more than what was on the scoreboard.

The Island Cup game has been rescheduled to Sunday at 2 p.m. on Nantucket. The fan boat leaves the Vineyard on Oct. 31 at 7 a.m. Field hockey and boys and girls soccer also play at Nantucket that day.

In a disappointing Friday night under the lights, the VIneyard football team fell to the Sharon Eagles at home in overtime, 15-7.

In a heart-breaking, back-and-forth football game, the Vineyarders fell 8-6 in overtime to the Salem Witches on Saturday during the first home game of the season.