The 1999 Chatham Cup was the 72nd annual nationwide knockout football competition in New Zealand.
Up to the last 16 of the competition, the cup was run in three regions (northern, central, and southern), with an open draw from the quarter-finals on.
Note: Different sources give different numberings for the rounds of the competition.
[citation needed] Dunedin Technical made up for their big loss in the 1998 final, winning 4–0.
The winner of the 1999 Jack Batty Memorial Cup was Aaron Burgess of Dunedin Technical.