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.
Eight regions that were represented last season, chose not to participate in the competition among which are such oblasts Chernivtsi, Dnipropetrovsk, Kirovohrad, Mykolaiv, Vinnytsia, Zakarpattia, Zaporizhzhia, and Zhytomyr.