The 1999 Ukrainian Amateur Cup was the fourth annual season of Ukraine's football knockout competition for amateur football teams. The competition started on 6 September 1999 and concluded on 16 October 1999.
The competition shifted to spring-fall system (within a single calendar year) along with competition in championship.
The cup holders HPZ Varva were defeated at semifinals by Shakhta Ukraina Ukrainsk.
In bold are clubs that are active at the same season AAFU championship (parallel round-robin competition).
The following is the bracket that demonstrates the last four rounds of the Ukrainian Cup, including the final match. Numbers in parentheses next to the match score represent the results of a penalty shoot-out.