Victory, to Martha’s Vineyard schools superintendent Dr. James H. Weiss, tastes like chocolate-covered cranberries.

But to Nantucket schools superintendent W. Michael Cozort, victory tastes more like Tashmoo truffles and almond butter crunch from Chilmark Chocolates.

On Saturday, when the Vineyarders face-off against high school football rival Nantucket for the annual Island Cup, the two school superintendents will be in the stands on their respective sides, each holding a box of Island-made chocolates.

“We wager chocolates,” Mr. Weiss told the regional high school committee earlier this month. “The Nantucket superintendent and I go back many years, back to our New Hampshire days.”

“It’s true,” Mr. Cozort told the Gazette by telephone Thursday morning. “It’s good fun. I think you know how rivalries can be and how they can sometimes be heated, but I think he and I have a pretty good perspective on it.”

The friendship between Mr. Weiss and Mr. Cozort began two decades ago when they both served as school superintendents in New Hampshire.

Then five years ago, Mr. Cozort accepted a job as Nantucket schools superintendent, reconnecting him to his old buddy Mr. Weiss. “We’re both Island guys now and appreciate the advantages and challenges of education on an Island,” Mr. Cozort said. “It’s nice having him to run things by.”

And it’s even nicer, he said, to have a friend on the other side to shake hands with at halftime of the Island Cup.

“Our friendship is deeper than the rivalry,” Mr. Cozort said.

As for who will win this year, it’s hard to tell; both superintendents are hungry.

“I’ve been here for nine years and so far, the Vineyard has won every game,” Mr. Weiss said. “I hope the Vineyard wins. I’m ready to eat chocolate!”

Saturday’s game is also the last for Mr. Weiss as superintendent; he is set to retire at the end of the school year.

“We would like nothing more than to send him off with one loss in his belt,” Mr. Cozort said with a chuckle. “We’ll see, the game has been competitive in the last three or four years. That’s why we play the game, you never know what will happen.”

There is one thing Mr. Weiss and Mr. Cozort agree on about the game on Saturday: victory is sweet.