The annual Island Cup game between the Vineyard and Nantucket football teams has long been a high-stakes affair, played to the bitter end for the right to dominate the world — or at least bragging rights between the two Island rivals.

And until six years ago the Whalers won the game on a regular basis. From 1993 to 1998 Nantucket won five out of six, and four in a row over the Vineyard.

But things have turned around. Under coach Donald Herman, the Vineyarders have now won five games in a row with a chance for a sixth tomorrow when the tradition is renewed on Nantucket.

How things have changed. Six years ago Nantucket quarterback Matt Erisman hit wide-out Ryan Sosebee for a 47-yard touchdown to seal a 25-20 Whaler win in the 2002 Island Cup game.

In that game, quarterback Eric McCarthy drove the Vineyarders to within the Whalers 20-yard line with under two minutes with a chance to give his team the win.

And although things have changed for the two teams, some names remain the same.

When the Vineyarders take the field tomorrow they will be led by senior quarterback Mike McCarthy, younger brother of Eric who led the team to a near victory six years ago. Mike is having one of the best seasons ever for a Vineyard quarterback, scoring 31 touchdowns and racking up over 1,000 yards total on offense.

But names and final scores aside, the overall texture of the game has changed in recent years. The two teams formerly played in the same division — the Mayflower League Large — and from 1990 to 2001 (and again in 2003) the winner of the Island Cup game went on to play in the Massachusetts Interscholastic Athletic Association divisional Superbowl.

Two years ago Nantucket moved to the Mayflower League Small due to declining enrollment, and the team has struggled as more student athletes have opted to play other sports like soccer. And while the Vineyarders this year put together a banner season, going 9-1 overall and a perfect 6-0 in the Mayflower Large, earning a berth in the Division 3A playoffs, the Whalers have gone in the other direction, compiling a dismal 0-7 record overall.

The Whalers have had problems filling their roster. In a recent game against Old Colony, Nantucket dressed only 13 varsity players for the game and brought four freshmen as emergency back-ups in case of injury. They recently lost two starters to academic ineligibility, two more to disciplinary suspensions and others to lingering injuries, leaving the remaining squad thin and relatively inexperienced at the varsity level.

Hard to imagine that it was only four years ago when the now-famous “water boy” game was played on Nantucket, when the Vineyarders won thanks to a 29-yard field goal by E.J. Sylvia to give the visitors a 21-20 come-from-behind win. Many remember that game for the closing seconds when players, fans and a wayward water boy had to scramble off the field during the Whalers’ last-second kickoff return.

Nantucket athletic director Chris Maurey said this week the disparity between the two teams has grown to the point where he even thought about cancelling the game — not because the Whalers chances of winning are slim but because of the risk of injuries. He said only 16 or 17 players are dressing for the game, far fewer than previous Island Cup games.

“To be honest I’ve had a lot of sleepless nights wondering if this game should even be played,” he said.

But he said cancelling the game would have too many negative repercussions.

“It’s something people look forward to each year; it’s our homecoming; it’s a tradition. This rivalry is something we want to keep alive,” he said.

Mr. Maurey said he had discussions with Coach Herman and Vineyard athletic director Mike Joyce about his concerns about the game. He said he left those discussions with a feeling they understood his team’s limitations.

“Obviously there is a level of trust and respect that goes into this. I have talked to Don [Herman] and Mike [Joyce] and told them exactly where our program is right now. I live my life by [the belief] that you do unto others as you would want done onto you, and I think that can be applied here,” he said.

Mr. Joyce said this week that Coach Herman and the other coaches are aware the Nantucket team has a reduced roster. “We understand they are struggling. And if you are a coach worth anything you understand that when you’re up three touchdowns late you make sure all the kids get to play,” he said.

Although Nantucket is a clear underdog, interest in the Island Cup remains strong.

Jack Law, president of the Touchdown Club, the team’s nonprofit booster club, said tickets for the fan boat have been selling at a brisk pace. He said the game will always generate hype because of the history and long rivalry.

“As the game gets closer people always get excited . . . even this year. People remember those previous games and they want to be a part of history,” Mr. Law said.

Bob Tankard, a former player and head coach of the Vineyarders, said this year’s Island Cup may have lost some luster, but not its popularity. He said he genuinely hopes Nantucket improves and the two teams will be more closely matched in the future.

“I was talking to a guy the other day and he said the rivalry can’t stop because the Vineyard still has a ways to go to catch up with Nantucket [in total wins]. And that’s how it goes . . . up and down. When the two schools first started playing the Vineyard dominated, and then coach Vito [Capizzo] came and they started beating us every year.”

He continued: “Now with Coach Herman it’s our turn to win. . . and there’s nothing to say things can change again.”

Mr. Tankard said he hopes the rivalry lives forever.

“It’s a tradition for the fans and a rite of passage for those kids. It’s something they look forward too and something they will always look back on,” he said.