When it comes to local rivalries, nothing stirs up emotions like the coveted Island Cup. Since its inception in 1978, the football matchup between the Nantucket Whalers and the Vineyard has become a cornerstone in each of the Islands’ respective cultures.
This year, to much fanfare, the intense rivalry between the two football programs has earned the attention and accommodation of one of New England’s favorite sports venues — Fenway Park, where the Island Cup will be played on Nov. 26.
And there’s a lot at stake. The Whalers haven’t won the Island Cup since 2021 when they beat the Vineyard 27-7 on Nantucket. The Vineyard so far has won 22 Island Cups to Nantucket’s 21.
The Vineyarders, at least on record, are the stronger team. They are entering the matchup boasting a 6-4-1 record, on the heels of their second consecutive Cape and Islands Lighthouse League Championship. Led by a strong defensive line, and standout offensive performers, they are aiming to secure their third straight Island Cup victory on Tuesday at Fenway.
Across the water, a new era has begun for the Nantucket High School’s football program this fall with head coach Reese Everett taking over as the new leader. The Whalers finished their season with a 3-8 record. While they may have a worse record, they are coming off a decisive road victory over the Hull Pirates, 35-7. The Whalers knew entering the season this was a bit of rebuild, and they know they can take another step towards getting back to where they want to be as one of the Cape & Islands premier programs by bringing the Island Cup back to Nantucket next week.
With both teams preparing to showcase their talents at Fenway, the matchup appears evenly poised. The victor will likely be the team that can maintain composure and focus amidst the intense pressure of the historic rivalry and the iconic venue.
For Vineyard fans traveling from Island, Jen Royal and Kim D’arcy from the Island’s touchdown have put together a travel guide including links to different ticket booths, community bus registration, and information for the pregame party at Loretta’s Last Call.
Head to head:
The Whalers will be led by junior wide receiver Arann Hanlon (No. 11), who has established himself as one of Nantucket’s most dangerous offensive weapons while also being a very formidable defensive back. Hanlon scored seven touchdowns last season as a sophomore. Hanlon’s blend of shiftiness and explosiveness makes him a dynamic player. Expect to hear his number called quite a bit at Fenway.
On the Vineyard side, Guillerme Oliveira (No. 1) is a versatile offensive powerhouse. Whether taking on positions like running back, fullback, and receiver, Oliveira’s explosive speed makes him a threat to break tackles, creating big gains on wide sweeping plays. He can also power through defensive gaps on isolation plays. Expect to see the ball in Oliveira’s hands a lot.
Nantucket has been unsteady at the quarterback position this season. Due to an injury-plagued season, Freshman quarterback Burke Lombardi (No. 7) has taken a lot of snaps and gained valuable experience as the future of the Whaler’s program. While young, he’s made some big plays and he isn’t afraid to stand in the pocket and deliver a strike with a defender barreling down on him.
For the Vineyarders, Junior Quarterback William Nicholson (No. 10) is a mature and steady leader. The Vineyard’s passing game has shown some inconsistencies this season, which has led to turnovers. But Nicholson can deliver a solid passing game and he has proven to comfortably scramble in the slot sometimes opting to take yardage on his own where he finds fit.
Wild Card: For the Martha’s Vineyard football program, their defensive line has been paramount to this season’s success. Despite being considered undersized, the purple and black wall has delivered critical holds in high-pressure moments, keeping games within reach. Their speed and strength, depth and versatility set them apart. In contrast, the Vineyard’s offensive line has faced challenges with consistency.
See a PDF page of our head-to-head preview in Thursday’s paper.
