The storied Island Cup has roots reaching back more than 60 years, to the first time Martha’s Vineyard and Nantucket faced off on the football field. Nantucket won that first match, 33-22, and a rivalry was born.

This week the Vineyard Gazette has added a new collection on Island Cup history to its digital archives. The collection on the Time Machine section of the Gazette’s website features a timeline of Island Cup history and stories and photographs documenting the inter-Island football rivalry, back to 1953.

Through the years, the Whalers and the Vineyarders traded winning streaks as the Island Cup slowly gained national attention. The Time Machine collection recounts the 1995 game, when four skydivers jumped onto the field to present the game ball, and the 2009 contest that wasn’t, as Nantucket called off the game because of the travel expense.

Soon the 2016 game will be part of this history, and the collection will be updated to reflect the winner of the 38th Island Cup, held this year on Martha’s Vineyard.

The Time Machine is part of the Gazette’s multi-year project to digitize the Vineyard Gazette’s archives and make Vineyard history more accessible.

Other collections explore the history of the fishing derby and African American history on the Vineyard, as well as Steamships and Ferries, Presidential History, Historic Movies, Gazette History, and Hurricanes and Storms. More collections will be added in the months and years ahead.

Those with suggestions or additions for the Time Machine can contact librarian Hilary Wall at Visit the Time Machine at