The year was 1980 and the Vineyard had just broken a long streak of Nantucket wins. Head football coach John Bacheller and assistant coach Bob Tankard thought it would be a good idea to commemorate the occasion.

“We ordered the cup from Falmouth Trophy, went over by boat and picked it up,” Mr. Tankard recalled. The trophy was on the Vineyard for 12 too-short months: “The next year, we had to give it back.”

When Mr. Tankard was a player, there was no prize in this storied annual footbal game other than bragging rights. He has viewed the inter-Island rivalry through three separate lenses: as a halfback and safety on the squad from 1961 to 1964, as an assistant coach under Mr. Bacheller, and as head coach from 1981 to 1987.

When Mr. Tankard was on the squad, the team played Nantucket twice a year. In 1962 and 1963, the Vineyard won both contests. The 1963 team was a powerhouse, posting an undefeated season and allowing six points in the six-game season. Two of the points came against Nantucket, on a safety. The final score of that game was a somewhat absurd 2-0. He recalled the scrappy win to cap an unbeaten year was an enormous boost to the Vineyard players, particularly the seniors, revealing to them what they were capable of accomplishing as they entered adulthood.

The Vineyard defeated Nantucket only once while Mr. Tankard was head coach, on home turf in 1985.

“We had a latency period,” he said. “Nantucket just became . . . they were just powerful.” The Vineyard squad that took home the win was coming off a 5-4 season. “We ground out the game and it was unbelievable; the team that we beat them with wasn’t necessarily the best team we ever had. They were almost like the Red Sox team was this year. They did a lot of things together, did whatever it took to win.”

Nantucket coach Vito Capizzo had been so confident the Whalers would win that year, he didn’t bring the trophy across the Sound for the game. It had to be sent over the following Monday.

As a coach, Mr. Tankard sought to give to his players what his own coaches, Dan McCarthy and Maury Dore, had given him.

“I always looked at us as role models,” he said, recalling that as a player he had thought “I want to do that; I want to help these people.”

“It was about giving young men a chance to succeed in life,” Mr. Tankard said. “You get knocked down, you gotta get back up. If you can learn to get knocked down, to come back from defeat . . . that was fully my goal.” Mr. Tankard’s commitment to this aim didn’t just extend to the Vineyard players. Once, after the Vineyard soundly defeated Old Colony in a home game, he gave the Old Colony players a pep talk while they were on the ferry back to the mainland. Years later, the Old Colony coach still remembered the talk.

“You put everything in to win,” Mr. Tankard told the players. “That’s what I want you to take away from the game.”

And that’s what stands out the most to him about Island Cup games: The complete commitment and focus players have.

“The whole season gets thrown out the window,” he said. “We gotta keep the Cup.” Last year was a tough game. This year? “Another battle,” he predicted.

“Everybody plays at another level,” he said. “It’s the last thing, there’s no next week.”