The Island Cup, the storied inter-Island battle between the Vineyard and Nantucket high school football teams that comes around every November, will have a markedly different feel this year. Nantucket coach Vito Capizzo, who is as storied as the rivalry, announced this week he is retiring after 45 years.

Mr. Capizzo is one of the most successful high school football coaches in Massachusetts history, having amassed an astounding 293 wins over four decades and leading the Whalers to nine Super Bowls, including championships in 1980, 1995 and 1996. The team also regularly defeated the Vineyard in the annual Island Cup game through the 1980s and 1990s.

But the team has fallen on hard times in recent years, going 0-10 last season, the first winless season since Mr. Capizzo’s first year as coach in 1964. The balance of power for the Island Cup has also tilted heavily toward the Vineyard, which has won the cup the last six years in a row and nine out of the past ten years.

Vineyard coach Donald Herman had warm words of praise for his colleague on Nantucket this week. “It’s going to be strange looking over there and not seeing the old [guy] along the sidelines,” he joked, quickly turning serious. “Vito has had a great career. He started coaching that team when I was only five years old; which is incredible, if you think about it . . . it reminds me I have a long way to go.

“Even on the Vineyard, people understand what a good coach he was. He will be missed.”