Island Cup

October 2, 1953

Football Debut Is Eagerly Awaited

Vineyard Gazette
The debut of the first Vineyard football team, under the guidance of Coaches John Kelley, Daniel McCar­thy and Stanley Whitman, will take place tomorrow afternoon on the newly laid-out field at t
Island Cup
Football
October 29, 2022

Vineyard Takes Back Island Cup, Beating Nantucket 14-13 in Thriller

Aaron Wilson
For the first time in six years, the Island Cup is staying on the Vineyard. In a battle of wills, the Vineyarders outlasted Nantucket 14-13, holding their rivals scoreless in the second half.
Island Cup

2000

November 17, 2000

Island Rivalry: Football Team Battles for Cup On Nantucket

Cole Louison
Island Cup
 
Saturday’s game for the Island Cup is one of the most-storied high school rivalries in the country, and the defining moment for a Vineyard culture that flourishes for three months every year.
 
But unlike the shedding trees or shrinking afternoons that mark the end of what is arguably one of the nicest times of year on the Island, football season goes out with a bang.
 

1999

November 26, 1999

Vineyard Crushes Weak Nantucket Team On the Road to State Super Bowl Final

Bryan Chambala
Island Cup
 
The Cup is home.
 
Sparked by the spirited play of junior Jeff Lynch and his two touchdowns, the Martha’s Vineyard football squad recaptured the Island Cup last Saturday, defeating Nantucket 38-12. The win marked the end of the Vineyarders’ perfect 10-0 regular season and secured them a spot in the Division 5 Super Bowl on Dec. 4 at Boston University.
 

1998

November 27, 1998

Vineyard Loses Nantucket Heartbreaker

Scott Smith
Island Cup
Football
Regional High School
 
As Vineyard coach Don Herman arrived at Nantucket’s football field carrying the Island Cup last Saturday, a couple of fans wearing Nantucket sweatshirts jokingly offered to take it from him. Coach Herman smiled politely, clutched the Cup a little tighter, and kept walking.
 
Nantucket’s team was finally able to wrest the Cup from the coach’s grasp, but it took all 40 minutes of the game to do so. In a brave effort, the Vineyarders came back from a 21-6 halftime deficit to tie the game before Nantucket prevailed by the final score of 27-21.

1997

November 28, 1997

Big Win Sends Vineyard to Super Bowl

Marcus C. McGraw
Island Cup
Football
 
They completed an 11-0 season. They are league champions. And they have already danced with a trophy over their heads in front of a home crowd. Yet, there is still one element needed before the Vineyard high school football team can call this a perfect season. 
 
A Super Bowl victory.
 

1996

November 29, 1996

Vineyard’s Narrow Loss to Nantucket Is Tantalizing Tale of What Might Have Been

Jason Gay
Island Cup
 
NANTUCKET - If not for a couple of yards, it might have been a game for the ages, recounted in coffee haunts, barber shops and summer barbecues for generations to come.
 
But when Martha’s Vineyard high school quarterback Mike Snowden fumbled the ball in overtime on the Nantucket two-yard line Saturday, another great Island Cup showdown was over and the Whalers escaped with a 13-7 win.
 
This was a bizarre, hard-fought game with more strange twists than an Elmore Leonard thriller.
 

1995

November 24, 1995

Superbowl-Bound Nantucket Football Team Defeats the Vineyard

Jason Gay
Island Cup

They came, they saw, they squished.

Using their clumsy "Squish the Grapes" battle cry, the Nantucket Whalers rumbled into Oak Bluffs Saturday and pounded the Martha's Vineyard high school football team 30-13 in a predictable, impressive triumph. The victory before 2,500 Island fans marked the third consecutive Island Cup win for the Super Bowl-bound Whalers.

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