Nantucket used to be Ken Goldberg’s second favorite island. But after calling Martha’s Vineyard Regional High School football games for 33 years, our sister island has dropped to number five on his list of favorites.

The Vineyard is number one, of course, followed by Manhattan, Coney, St. Simons, Ga. And Nantucket.

This year on the Saturday after Thanksgiving Ken Goldberg will be on his fifth favorite island again, calling the Island Cup football game in a live broadcast for MVTV.

“It’s truly a tale of two Islands,” he said in a recent interview, wearing his purple varsity letter jacket and purple plaid shirt. A purple sweater his mother knitted for him lay nearby. One side is stitched with the letters MV stitched and the other side KG. He only wears it once a year.

“When you get to the Nantucket-Vineyard game, forget what the season records are,” he said. “It’s a great rivalry.”

Between football, boys hockey and baseball, Mr. Goldberg estimates he has broadcast or filmed about 800 sporting events over the years for WMVY and MVTV, calling out the names of multiple generations of Island families.

And he remembers nearly every game, every key play, every defining moment.

Take 2004, for example.

“E.J. Silvia kicks a field goal with three seconds left and the Vineyard comes back to win 21 to 20, the only play left in the game is the kickoff,” Mr. Goldberg said. “EJ kicks the ball off and a kid from Nantucket catches the ball and gets surrounded. From my vantage point he gets knocked down to the ground and the game is over and the referee should blow the whistle.”

But there’s no whistle.

“The kid gets up and pitches the ball to somebody else and that kid is running down the field for a touchdown,” he continues, leaning into the story. “I can’t believe this but everyone else on the field must have thought the game was over because all of the spectators were running on the field. The kid from Nantucket has a break away . . . when our waterboy accidentally runs in front of the kid from Nantucket. He has to slow down so we tackle him and the game is over.”

Mr. Goldberg was a gym teacher at the Oak Bluffs school when he responded to an advertisement from WMVY in 1981.

“I went down [to the high school] and there were about a dozen other fellows there at the time,” he recalled. He volunteered to be the first to sit behind the microphone and call a scrimmage.

“They didn’t have real uniforms on but I knew the kids so I started calling the game,” he recalled. “I did the game for five or 10 minutes and stopped.”

“All 10 other guys walked away,” he laughed. “So I got the job.”

Founded in 1978, the Island Cup rivalry began to heat up in the mid-1980s, he said. The 1984 game on the Vineyard stands out in his memory. That was the year his radio personality got away from him.

“We were playing here on the Vineyard and Erik Blake was about 40 pounds heavier in high school,” he said, referring to the man who is today Oak Bluffs police chief. “The Vineyard is leading six to two and Nantucket fumbles. Erik picks the ball up and takes off for a touchdown and scores. And I get a little excited broadcasting and remember yelling, look at that porker run — I couldn’t remember Erik’s name.”

This year the game is on Nantucket, and Mr. Goldberg will be there.

“Watch your wallet on Nantucket,” he smiled.

But when it comes to longtime Vineyard coach Donald Herman, there are no jokes, only warm words of praise.

“Football really requires a team effort and I’ve seen a lot of coaches,” Mr. Goldberg said. “The fact that over the years a number of former players have come back and acted as assistant coaches indicates their love for the program.”

The Vineyard is not favored to win this year, but Mr. Goldberg repeats the mantra: season records hold little sway in the Island Cup.

“They’re not very large but I’ve never seen a team play as hard as this team,” he said. “They’re matched against some really tough teams, and despite the knockouts, they’ve worked really, really hard. I think it’s a testament to the coach and the players.”

He ends the broadcast of every game the same way, a tradition that dates back to when he called the game with his partner Norman Vunk, who has since retired from broadcasting games.

“Years ago when Norman was doing the game we wrapped up the final score and I said, ‘Say good night Norm.’ And he went, ‘Goodnight Norm.’ We’ve said it ever since.”

Mr. Goldberg said every year is his last year, but even he says don’t believe it.

“I’m not quite ready to say good night Norm.”