The tournaments were first proposed in 2018 in response to the folding of the KPAQT by former Smithtown West player Joe Feldman; after a year of preparation, the tournaments began in October 2019. Each leg is a direct successor to a discontinued Long Island tournament: the October leg is the successor to SWISS; the February leg is the successor to KPAQT; and the May leg is the successor to the long-discontinued Hills West tournament.
The inaugural event was widely mocked as the "Meme Tournament" due to the small field. Reviews for the February 2020 event were highly positive. Notably, the event featured four teams from Connecticut in the top bracket, despite the "Island Cup" moniker.
The May 2020 event was moved to Discord in response to the Coronavirus pandemic on Long Island. It was the only tournament to make such a move.
Island Cup Trophy
The top team over the three tournaments from Long Island (i.e. Nassau and Suffolk counties) is awarded a silver-coated pewter traveling trophy. Being that results from three tournaments are taken into consideration, the winner is determined by a points formula.
- For every win in the prelims, teams earn one point;
- For every win in the playoffs and finals, teams earn two points;
- For every loss in the playoffs, teams earn one point;
- For every win in the First Consolation bracket, teams earn one point;
- For winning a tournament, teams earn three points, two for second, and one for third;
- For every prelims loss, second-and-lower consolation win, or consolation loss, teams earn no points.
|#||Date||Location||Set||T||Champions||Second Place||Third Place||Fourth Place||MVP|
|I||Oct 2019||Great Hollow MS||IS-187A||10||Kellenberg A||Churchill JHS A||Island Trees A||North Babylon A||Aidan York, Kellenberg A|
|Feb 2020||Great Hollow MS||IS-191A||16||Darien B||Darien A||West Egg A||Middlesex MS A||John Phipps, Darien A|
|May 2020||Discord||BUTTERSCOT||26||Wayzata||Scarsdale||Canada NB||Kinkaid||Jacob Hardin-Bernhardt, Team Pierre Trudeau|
|Island Cup||--||--||45||Kellenberg A||Darien B||North Babylon A||Darien A||Jacob Hardin-Bernhardt, Team Pierre Trudeau|