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.

For the first time in history, the Island Cup will be played at Fenway Park, with the Martha’s Vineyard Regional High School football team heading to Boston this year to take on the Nantucket Whalers in the longstanding tradition.

The Vineyarders won the Island Cup for the second year in a row, with a dynamic 24-21 win over the Whalers. The boys and girls soccer teams were also victorious Saturday, each winning an inaugural Golden Anchor trophy.

Vineyard sports teams travel to Nantucket this weekend for the Island Cup and the new "Battle in the Atlantic" tradition.

Island Cup bragging rights will not be the only trophy on the line this Saturday when Vineyard sports teams travel to Nantucket. This year the field hockey and boys and girls soccer teams will do battle for the Golden Anchor trophies.

For the first time in six years, the Island Cup is staying on the Vineyard. In a battle of wills, the Vineyarders outlasted Nantucket 14-13, holding their rivals scoreless in the second half.

The ultimate inter-Island rivalry is rekindled this week, as the Martha's Vineyard Regional High School prepares to host Nantucket in a slate of fall sports contests culminating Saturday in a battle for the coveted Island Cup.

On a windy Halloween day on Nantucket, the Whalers cruised to a 27-7 victory against the Vineyarders in the historic Island Cup rivalry.

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.

The Island Cup football game between Martha’s Vineyard and Nantucket has been canceled due to exposure to Covid-19.