The current champions of the Chatham Cup are Wellington Olympic, who defeated Auckland City on penalties in the final.

Typically between 120 and 150 teams take part, with extra time and penalty shoot-outs used to decide matches which end in ties.

In the past, replays were used, and in the early years of the competition the number of corners won during a game decided tied matches.

The cup, which cost £150, was presented to NZFA President Sir Charles Skerrett by Captain Cecil Burnaby Prickett on board the Chatham on 14 December 1922.

Most of the competition's winners have come from the main centres of Auckland, Wellington and Christchurch, though teams from Dunedin, Gisborne, Hamilton, Masterton, Nelson, and Napier have also won the competition, while the inaugural champions were from the small settlement of Seacliff, with many of the team being staff from the nearby psychiatric hospital.

The clubs themselves received only a tiny percentage of the money made in gate takings, and often had to travel considerably further to play matches than they did in the provincial leagues in which they competed.

Concerns as to the costs involved and the limited financial support from the NZFA for entrants in the competition led to some teams disbanding as a result of the debts incurred, notably early winners Harbour Board.

The trophy honours Jack Batty, who was both a member of the crew of HMS Chatham and also a three-time medallist in the early days of the tournament with Auckland Harbour Board, Tramways, and Tramurewa.

In September 2023, New Zealand signed a deal to have select Chatham Cup games streamed for free on FIFA+ worldwide.