The annual Island Cup football rivalry between Martha’s Vineyard and Nantucket is set to return this weekend, a year after it was cancelled for only the second time in its long history, dating back to 1953. This year’s matchup takes place Saturday, Nov. 17 beginning at 1 p.m. at Nantucket High School.

Last fall, injuries and disciplinary issues plagued the Vineyarders throughout the season, forcing first-year head coach Ryan Kent to call off the game. The only other time the storied matchup was canceled was in 2009 when Nantucket declined to schedule the game because of financial issues.

For Vineyard coach Donald Herman, who returned to the helm after a two-year retirement, this year’s matchup is a chance to reclaim the coveted Island Cup trophy that’s resided on Nantucket the past two years.

“It’s good to be back,” he said. “I told the team don’t worry about what’s happened in the past. Focus in on what you can do this week. I’m trying to make sure they understand just how important this game is to the school and the community.”

Nantucket currently leads the rivalry 36-30, with three ties. The first game in 1953 was played when the Vineyard formed a team with what at the time included three high schools, in Edgartown, Tisbury and Oak Bluffs. (The actual Island Cup trophy was created in 1978.)

The Whalers won the inaugural game on their home field 33-20 after an injury-filled game that included a twisted ankle, dislocated thumb and a broken nose.

The Whalers dominated the rivalry until the early 2000s under Coach Vito Capizzo, after which the Vineyarders held the trophy for a record 12 straight years under Coach Herman’s leadership. The streak ended in 2016, the year after Mr. Herman retired, with a 42-0 blowout loss at home, the most lopsided game in Island Cup history. The Vineyarders head into the Island Cup this year coming off a disappointing 2-8 regular season where the young team struggled to gain momentum but showed signs of future success in several close games. The Whalers finished the regular season 6-2, reaching the Division 7 South Sectional semifinals where they lost to Abington High School.

Mr. Herman, who’s led the Vineyarders in 27 Island Cups, said none of that matters when the two squads meet on the gridiron Saturday for Island bragging rights. “Records go out the window for the Island Cup,” he said. “We’ve had a 10-game preseason, and now we have a one-game season. Everything that we’ve tried to teach and incorporate into the year has built up to just this one game.”

During a windy and muddy practice Tuesday afternoon, Mr. Herman stood behind his defense with his arms crossed and a whistle in his mouth. He blew it and a running back holding the football dashed to the side of the field trying to avoid a defensive back charging at him.

“Attack his outside shoulder,” Mr. Herman yelled. “They like to go outside!”

The defensive back caught the running back just before he turned the corner. Mr. Herman blew the whistle again and the drill reset. He looked down at page one of his practice schedule packet and shook his head.

“This game is the creme de la creme of the year,” he said. “They aren’t ready yet, but I don’t want them ready yet. It’s too early in the week. If they’re ready now they’ll run out of energy by

halftime. There’s a different focus this week, more attention to detail.”

Mr. Herman said it was tough to watch from the sidelines when Nantucket ended his Island Cup winning streak in 2016.

“All good things come to an end,” he said. “We had it for 12 years. Hopefully, it won’t take that long to get it back.”

A new drill began and Mr. Herman and the team crossed over to the other side of the field. A black sticker adorns the back of each helmet with the initials VC in white. Mr. Herman said this is to honor Coach Vito Capizzo, who died earlier this year, making Saturday’s game the first without Mr. Capizzo looking on from either the sidelines or the stands. Mr. Capizzo led the Whalers for 45 years and to nearly 300 career wins before he retired in 2009.

“He was a good competitor and good friend,” said Mr. Herman.

First-year Nantucket coach Joseph Perry agreed that Mr. Capizzo’s spirit will be part of the game Saturday.

“Vito is legendary here,” he said. “It means a lot to me to be on the sidelines where he once stood.”

Mr. Perry said he’s glad the rivalry is back on and though he and Mr. Herman call each other friends, he plans on Nantucket keeping the Cup indefinitely.

“We agree to disagree just one day out of the year,” he joked. “I hope it’s a good experience for both teams on the field and a good experience for both islands. Football brings us together.”

This year’s Island Cup also marks the last year the game will be played in November at the end of the season. Next fall the Vineyarders will move from the Eastern Athletic Conference back into the nine-team Cape and Islands League that includes Nantucket. The game will be played earlier in the season per league requirements, making it a matter of more than just pride for the two teams, since winning the game could also mean winning the league.

“That adds to the flavor,” said Mr. Herman.

Last Friday at practice, Mr. Herman resumed a tradition he started in 1991. The senior players gathered in the end zone and then every coach and every player took turns shaking their hands, and congratulating them on their high school football careers. Mr. Herman then handed a letter to the seniors and had them open it away from the rest of the team to read it.

“I give them a letter I wrote and assign a senior to read it,” he said. “It’s not for the coaches. It’s just for them.”

Mr. Herman said that regardless of all the history and circumstances surrounding this year’s Cup, on the field Saturday it’s just going to be about football and the fight for another yard on hostile territory.

“This game is played with so much emotion and intensity that everything that could happen will happen,” he said. “You never know what you’re going to see.”

Transportation to Nantucket is available via a Steamship Authority ferry chartered by the Martha’s Vineyard Touchdown Club, the Island’s football booster organization. The ferry will leave Vineyard Haven on Saturday morning at 7:30 a.m. and return from Nantucket at 4:30 p.m. Ferry tickets can be purchased at the MVRHS front desk or at Northline Shell. Adult round-trip passenger tickets are $30. Tickets for students and seniors are $20. Car reservations are sold out.