The record shows that in 1953, an informal team of Vineyarders played football against Nantucket High School, losing 33-20. A rematch the next year yielded a scoreless tie.
 
Five years later, in 1959, Martha’s Vineyard Regional High School opened its doors, bringing together under one roof the ninth, 10th, 11th and 12th-graders from all six Island towns. This school consolidation enabled the Island to field an interscholastic football team for the first time, and official competition against Nantucket High School began in 1960.
 
After lo these many years, the annual contest is still going strong. Saturday’s game at Nantucket marks the 54th meeting of the two Island high schools.
 
Over the years, the rivalry in our little corner of the world has drawn attention from such national media outlets as The New York Times, The New Yorker magazine and, just this Wednesday, USA Today.
 
There’s just something about Island football that draws attention.
 
“It’s a great, unique rivalry and event,” said Vineyard head coach Donald Herman. “Where else do you have two Islands that play football that have to travel by boat or plane to play?”
 
Perhaps taking a cue from storied college trophies like the Old Oaken Bucket and the Little Brown Jug, the teams got together before the 1978 game and created the Island Cup, a trophy that the victor keeps until the following year’s game. This year’s is the 25th contest in which the cup is at stake.
 
Before the Island Cup, the schools played 29 times over 18 years, including twice a year between 1961 and 1971.
 
Nantucket, led by legendary head coach Vito Capizzo for 40 years, has dominated the series over more than four decades, although the Vineyard has enjoyed a change of fortune in recent years, winning the three most recent contests and four of the last five.
 
While the Vineyard win in 1977 may have prompted the creation of the Island Cup, fans with longer memories will recall that Nantucket won the first seven cup games between 1978 and 1984, part of a 13-2 run from 1974 to 1988. The Whalers lead the Island Cup competition 1608 and the overall series 33-18-2.
 
“Nantucket used to whip up on us quite frequently, and made no bones about it,” said Norman Vunk, an Island contractor who has covered Vineyard football games for almost 20 years, first on radio and lately for local cable television.
 
In the early years, however, even after Coach Capizzo arrived on Nantucket in 1963, the rivalry wasn’t so one-sided. Nantucket won in 1960 and twice in 1961, but the Vineyard swept the next four games in 1962 and 1963. As late as 1967, the Vineyard led the series 7-6-2.
 
Dennis daRosa, whose family has run an office supply store in Oak Bluffs since the 1930s, spoke with the Gazette about some of the early teams, including the undefeated squad of 1963. A freshman at the time, he was the backup quarterback, and his older brother, Tony, was a senior.
 
The starting line, Mr. daRosa said, “looked like the New England Patriots.
 
“They were well over 200 pounds. The tackles were big, strong guys,” he recalled. “I weighed 150 pounds. It wasn’t just a high school illusion — they were tough kids.”
 
Mr. daRosa’s comments revealed how times have changed: back then, the Vineyarders couldn’t play 11-on­-11 in practice because there weren’t enough kids on the team. Now the Vineyard suits up more than 70.
 
At the time, Mr. daRosa said, there was a head coach and one assistant coach, versus today’s 10-man coaching staff.
 
The high school didn’t even have its own field. Through 1963, the team played at the War Veterans’ Memorial Park in Vineyard Haven, behind what is now the post office.
 
But the Nantucket games were always special, he said.
 
“If you could have lost every [other] game and beat Nantucket, it would have been enough to get you through the winter,” Mr. daRosa said. “We didn’t have a cup or anything — that came later — but we didn’t need a cup.”
 
Nantucket “had some big boys when I was a junior and senior; they were tough,” Mr. daRosa said. “In those days they’d stay over [the Friday night before the game], and we’d stay over there.”
 
Mr. daRosa alluded to some youthful hijinks: “It became prob­lematic — I won’t go into that — but you got to know the guys.”
 
His older brother agreed. “We used to travel the day before,” Tony daRosa said. “We got to know them a lot better. It became a real rivalry early.
 
“We took the boat, probably the Nobska,” he said. Two and a-half hours each way, it was quite the ride.
 
“You got to meet those people. You’d stay with the same family every year and then their son would stay with you.”
 
Bob Tankard, retired principal of the West Tisbury School played with the daRosas and later coached the team before Mr. Herman’s tenure.
 
“The kids today can’t stay over,” Mr. Tankard said. The end of the practice in the late 1960s, he said, ended the development of “real interpersonal relationships” between Vineyard and Nantucket players.
 
Beginning in 1968, Nantucket swept eight games over the next four years, the last of which marked the last time the Islands played twice a year.
 
The Vineyard won again in 1972 and 1973, but 1974 marked the beginning of another era of Nantucket domination.
 
“Vito did an excellent job cultivating a positive program,” Mr. Tankard said. “When Nantucket brought in soccer [in the mid-1990s], their program started to go down. But he had a dynasty for 15, 20 years.”
 
Dennis daRosa agreed: “They’ve been ruined by soccer over there. The joke was that Capizzo, whenever he saw a soccer ball, he’d steal it or pop it. But he’s such a great coach, he transcends that.”
 
In truth, a variety of factors have probably contributed to the changing football fortunes of the two schools.
 
Vineyard athletic director Glen Field said that Nantucket’s soccer program - which, as on the Vineyard, inevitably draws some athletes away from the football team - probably has some impact.
 
Others wonder if the Vineyard’s rising enrollment is a factor as well, although Mr. Field points out that proportionally, Nantucket High School has always been about half the size of the Vineyard high school.
 
“We’ve always been bigger,” agreed Coach Herman. “It never seemed to be a problem before.”
 
Coach Herman says the Vineyard’s football program for seventh and eighth graders has been a boon, too. This year’s seniors, he said, lost only one game in junior high school competition.
 
He also cited the support the team receives from the Martha’s Vineyard Touchdown Club and from the community at large. “We have some very solid support for athletics - for all the teams - for education, really for kids in general,” Mr. Herman said.
 
Inasmuch as these factors all play a role, the key may well be the coach himself. Since taking over the program in 1988, the series has split down the middle, 7-7. Under Coach Herman, the Vineyarders are 122-38 overall.
 
Coach Herman “pretty much turned the program around,” said Tony daRosa.
 
Whatever the cause, the team’s recent success has made the traditional rivalry more interesting, at least for Vineyarders.
 
Of traveling to Nantucket for the game, Mr. Vunk said, “Once you get to that field, there’s electricity in the air. You can feel it almost when you get off the plane and you hear all the people from Nantucket talking about the game. It’s very exciting.”
 
“I’ve seen a lot of kids come through the program,” he added. “I’ll never forget the first time we beat Nantucket over there [in an Island Cup game, in 1992]. That’s about the most excited I got for a football game.”
 
Mr. Vunk continued: “The competitiveness is there, but the rivalry has changed. I don’t think Nantucket wants to play us much anymore.”
 
Mr. Field, in his first year as athletic director, doesn’t agree: “The more I’ve learned about [the rivalry], the more it seems like it’s something that’s going to go on for a long time.”
 
“It’s a great environment to play high school football,” Coach Herman said. “It’s a hard game to replicate, with the emotions and intensity level. Both Islands gear themselves up.”
 
As for the game itself - this year and every year, Mr. Tankard said, “The Nantucket game is when you throw everything out the window because you never know what’s going to happen.