In 1988, head football coach Donald Herman had just started coaching at Martha’s Vineyard Regional High School and was unfamiliar with the Island Cup, the annual rivalry football game between the Vineyard and Nantucket. The game was scheduled to be played on Nantucket that year, so he went over to “the other island” early with the junior varsity team, meeting up with then-Nantucket coach Vito Capizzo to see what the Cup was all about.

“I thought it was unique,” Coach Herman remembered. “[Vito] went into the town and hung a football in Main street saying, ‘Main street is closed at 12; football game at 1.”

“They won over there, 14-nothing,” he said, “It was all sort of new to me; I didn’t have a real grasp of it.”

It wasn’t until the next year, when Martha’s Vineyard hosted the game — and won, 26-14 — that the importance of the Island Cup became clear.

“When I saw the outpouring of excitement and joy for when we won over here, that’s when it really started to hit me, what this game represented,” he said on Thursday.

Brandon Watkins in last year's contest. — Ivy Ashe

More than two decades later, the saga of the rivalry has been codified in book form — Boston Globe correspondent James Sullivan’s Island Cup was published this summer — and the game again has earned a spot in’s Great American Rivalry series. This Saturday the Island will again revel in the rivalry when the 34th annual Island Cup is played at the regional high school. Kickoff is at 1 p.m. The junior varsity and junior high games will be played at 10 a.m.

Donald Herman is now in his 25th season as head coach of the Vineyarders, heading into his 24th Island Cup game. (The 2009 Cup was canceled, “That’s still a sore subject, and always will be,” he said, only half-joking.) A win on Saturday would be his 202nd with the Vineyarders. It would also even the score. Since the Island Cup was officially instituted in 1978, Nantucket has won 17 meetings. Martha’s Vineyard has won 16. Last year, the Vineyard won by three points, 10-7, in a defensive standoff of a game.

Nantucket has not taken a Cup win since 2002, and the Whalers are 4-6 this year, a reverse of the Vineyarders’ 6-4 record. The win-loss column is deceptive, though.

“Records don’t mean a thing going into this game,” Coach Herman said. “It’s a one-day, one-game playoff and both teams are going to get out there; they’re going to be playing their hardest [and] hopefully at their peak.”

“You have to be prepared for the unexpected,” Nantucket head coach Bill Manchester, now in his second year with the team, said in a phone conversation this week. “[Last year] we knew the Vineyard had the double-wing [formation in its playbook] . . . we just didn’t expect them to run it the entire game. We’ve got to prepare for everything, whether it was something run two years ago or 10 years ago.”

Nantucket has been “up and down” all season, Coach Manchester said. Thirteen seniors graduated last year, and only eight are on this year’s Whaler team.

“We’re a very young program,” he said. “We’re slowly getting better.”

Coach Manchester felt that the Whalers weren’t physical enough in last year’s Island Cup, so he scheduled a more challenging non-conference schedule for the team this year. The team lost to powerhouses Blue Hills (a 9-1 team) and Millis (8-2) early on, but Coach Manchester was pleased with the Whalers’ late-season performances.

“We had a last-second win against West Bridgewater. Our guys just kept hanging around, hanging around, and we pulled it out in the end,” he said. The Whalers won that game 20-14.

Just this past week, in a 39-22 win against Old Colony, he said, “you could see some of our young guys step up and play some of their best football.”

The Vineyarders have had a similarly up-and-down season, largely because the team has been plagued by injuries since the beginning of the season, before they’d even had a chance to kick off in a game. Senior Nick Costello and juniors Tony Breth and John Henry O’Shaughnessy are still sidelined.

“We’ve had games where . . . I didn’t know kids weren’t able to play until literally three or four hours before the game,” Coach Herman said. “It’s been a huge year adjustment-wise, especially on special teams . . . that’s where the biggest issues lie.”

In the first game of the season, against Old Rochester, three starters had to sit out because of injuries, and four more went down in the Vineyard’s 25-0 loss. “We looked horrible,” Coach Herman said.

Celebration following Vineyard's 2011 victory — Ivy Ashe

But the Vineyard recovered enough to go on a four-game win streak in its next games, eking out a 28-26 win against former Mayflower League opponent Bristol-Plymouth, rallying from a 14-point deficit to defeat Brighton 45-38, taking a relatively straightforward 41-8 victory against Randolph and hanging on for a 21-14 win over Medford.

A 31-7 homecoming game defeat by Cardinal Spellman segued into league play in the always challenging Eastern Athletic Conference. The Vineyard’s first game was against Somerset, a team that is currently 9-1. Somerset has 27 seniors on their team; the Vineyard has 32 varsity players total. The game ended in a 47-8 loss.

A similar fate met the Vineyarders when they took on Bishop Feehan and lost 47-8. The losing streak was broken in a Nov. 2 home game against Bishop Stang, a showcase of the Vineyard offense that ended in a 22-18 victory. The struggling defense, still working to adjust to new starters, came into its own with key fourth quarter plays. The win also happened to be Coach Herman’s 200th with the Vineyard program.

Prior to the Bishop Stang game, Coach Herman also made a deal with his team that if they could finish the season 7-4, he would shave his mustache after the game. Similar deals were made — and seen through — with the 1989 team, when he won his first Island Cup and finished 9-1, as well as with the 2003 team, which won the division Super Bowl.

“So there’s even more at stake [against Nantucket],” he laughed.

Last Friday, the team closed out league play with a 33-28 stunner over Coyle-Cassidy. Coyle-Cassidy jumped out to a 14-0 lead in the first half, but the Vineyard closed out the second quarter by scoring back-to-back touchdowns, taking advantage of a fumbled kickoff. Seniors Jahmari Thomas and Brandon Watkins scored two touchdowns each against Coyle-Cassidy, while junior Joe Turney notched one. Junior Kyle Stobie had 14 tackles to lead the defensive effort. In the last minute of the game, with Coyle-Cassidy up 28-27, senior quarterback Alec Tattersall connected with Watkins to secure the win.

“It was a heart-racer,” Coach Herman said of the game. “We did some things to make it tough on ourselves . . . I don’t think that game should have been nearly as close as it was.”

“If our guys come out with the energy level and the intensity and the focus as they did against Bishop Stang — and they’ll have to — I think they’ll be fine,” he said.