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.

“It’s going to be a busy campus,” high school athletic director Mark McCarthy told the Gazette this week. “I just feel like this is what homecoming should be.”

The rivalry between the Martha’s Vineyard and Nantucket football programs dates to 1953 — the first year the Vineyard pulled together an organized football team. A smattering of games were played between the two teams throughout the early years until the formation of the Martha’s Vineyard Regional High School in 1960, when the game became an annual tradition for both Islands.

The football team preparing for the game against Nantucket. — Ray Ewing

The titular trophy that is the Island Cup was purchased by Vineyard coach John Bacheller in 1978 during his second year as head coach, further legitimizing the fabled matchups between the two Islands. In a 2003 article printed in the Vineyard Gazette, Mr. Bacheller recounted a trip to the Falmouth Trophy Store to purchase the nicest trophy they had.

“I paid $127 for it. In those days that was expensive,” Mr. Bacheller said in the 2003 article.

Now, another Vineyard coach has a chance to leave his mark on the game. First-year head coach Tony Mottola has worked this season to rebuild the foundation of the high school’s football program, focusing on fundamentals with a gentle, instructional focus.

“We’re excited — it’s my first go around with this entire thing,” Mr. Mottola said. “I’m just soaking it all in.”

Mr. Mottola will lead the Vineyarders onto the field at 3 p.m. Saturday with a 1-6 record to face the 0-9 Nantucket Whalers. He said the team hopes to keep the game close and open up an opportunity for the Vineyarders to pull away in the fourth quarter.

“We’re just approaching it as another week where we’re just trying to be better as a team,” Mr. Mottola said.

Girls soccer seeks a playoff advantage. — Ray Ewing

This weekend also marks the first time the Vineyard will host the Island Cup under its new format, which sees contests between the Vineyarders and Whalers in nearly all fall sports. The inaugural event was hosted last year by Nantucket.

“To have them all playing at the same time, I think it’s going to be a really electric day up here,” Mr. McCarthy said.

Setting the pace for Island Cup weekend, the boys and girls cross country teams will host the league championships Friday starting at 2 p.m. at the high school. Coach Joe Schroeder said this week that the boys team will look to compete for the league championship and the girls, who do not have a complete team, will be vying for strong personal races and high individual placement.

“They’re psyched because they don’t have to travel,” Mr. Schroeder said. “You’re going to have to defend your home turf, which is fun.”

On Saturday, the boys and girls soccer teams and the field hockey team look to close out their seasons with wins against their sister island rival.

Field hockey teams play at 10:30 a.m. on Saturday. — Ray Ewing

“It’s going to be a very emotional game for us,” field hockey coach Becky Nutton told the Gazette. “It will be our senior game.”

The field hockey game begins at 10:30 a.m. at the high school, with a ceremony for seniors starting at 10 a.m.

“Nantucket is a really tough rival,” Ms. Nutton said. “They bring out the best in us.”

As the boys and girls soccer teams jockey for seeds in the state tournament, Saturday’s games have playoff implications for the Vineyard teams. Boys coach John Walsh said a win

against Nantucket would tie the team for a league championship, and could put them in position to play two home playoff games.

“We actually really care about this game because if we win, I think we get a share of the league title,” Mr. Walsh said.

The head coach said he’s anticipating a strong defensive game from the Whalers, and said the Vineyarders will work to outrun their opponent and capitalize on opportunities late in the game.

“They always give us a hard match no matter where we play them,” he said.

Bonfire on Wednesday evening kicked off Homecoming week. — Ray Ewing

The boys soccer game begins Saturday at 12:30 p.m.

The girls soccer team looks to secure a win Saturday in order to better their state ranking in hopes to skip a wildcard play-in game and earn a home-field advantage playoff game, coach Matt Malowski said.

“It could impact some of the seeding for the postseason,” Mr. Malowski said.

He added that the game, beginning Saturday at 10:30 a.m., will also serve as the senior game and holds emotional weight for the players as well as the coaches.

“It’s a big game for us,” Mr. Malowski said. “Big rivalry, all that stuff — it’s homecoming weekend.”

Marking the start of the Island Cup schedule, the high school hosted a bonfire Wednesday night, attended by teachers, coaches, players and students alike. With smoke billowing high above the school and the trees that surround the athletic fields, the Vineyarders prepared for the contentious weekend ahead, fanning the flames of a decades-old rivalry.

“I think either team can win,” Mr. McCarthy said. “We definitely have the ability to win.”