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 two in-person events lost thousands of dollars due to the small fields.
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.
For the 2020-21 season, the Island Cup was integrated into the American Quizbowl League, and the Cup was the Northeast regional October, February, and April online tournaments.
In 2021-22, the Cup was again administered by LIQBA. The first tournament garnered controversy for Feldman's handling of mask policy and his politics-related conduct, including his removal of two current events questions without NAQT's permission.
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.
|Num.||Date||Location||Set||Teams||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||Jimena Sarapura-Phipps, Darien A|
|May 2020||Discord||BUTTERSCOT||26||Wayzata||Scarsdale||Canada NB||Kinkaid||Jacob Hardin-Bernhardt, Team Pierre Trudeau|
|Island Cup I||--||--||45||Kellenberg A||Darien B||North Babylon A||Darien A||Jacob Hardin-Bernhardt, Team Pierre Trudeau|
|III||Oct 2021||Smithtown HS West||IS-205A||23||Livingston A||Mather A||Middlesex Middle A||Mather B||Aalok Bhattacharya, Staples|
|Feb 2022||Smithtown HS West||IS-207A||28||High Tech A||Mather A||Livingston A||Great Neck South||Robert Wang, Livingston|
|May 2022||Smithtown HS West||IS-210||26||Livingston B||Mather A||Greenwich A||Ward Melville A||Robert Wang, Livingston|
|Island Cup III||--||--||28||North Babylon A||Ward Melville A||Great Neck South||Kellenberg A||--|