The 2019 Chatham Cup (known as the ISPS Handa Chatham Cup for sponsorship reasons)[1] is New Zealand's 92nd annual knockout football competition.

[2] All teams listed below received byes to the first round.

[3] All teams listed below received byes to the second round.

All matches were played on Queen's Birthday weekend 31 May-3 June 2019.

[4] *The match between Mosgiel and West End was originally an on-field 5–0 win for Mosgiel but they were deemed to have fielded an ineligible player and the result was overturn to a 3–0 loss instead.