| Ukrainian Cup among amateurs | |
| Year: | 1999 |
| Country: |  Ukraine |
| Winners: | Shakhta Ukraina Ukrainsk |
| Second: | Troyanda-Ekspres Hirka Polonka |
| Continental Cup Title: | UEFA Europe League |
| Prev Season: | 1998-99 |
| Next Season: | 2000 |
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.
| Regions (Oblast) | Team | No. of participated seasons | Achievement | |
|---|---|---|---|---|
| Chernihiv | HPZ Varva | 1 | Winner | |
| Donetsk | Shakhta Ukraina | 1 | final | |
| bgcolor=pink | Ivano-Frankivsk | Korona Ivano-Frankivsk | Debut | none |
| Kharkiv | Krystal Parkhomivka | 2 | Final | |
| Khmelnytskyi | Dynamo-Orbita | Debut | none | |
| Kyiv | Chaika Vyshhorod | 1 | 1st qual | |
| Lviv | Rochyn Sosnivka | Debut | none |
| Regions (Oblast) | Team | No. of participated seasons | Achievement | |
|---|---|---|---|---|
| Luhansk | Ekina Almazna | 1 | 1st qual | |
| bgcolor=pink | Odesa | Syhnal Odesa | Debut | none |
| bgcolor=pink | Poltava | Psel Hadiach | Debut | none |
| bgcolor=pink | Sumy | Naftovyk-2 Okhtyrka | Debut | none |
| bgcolor=pink | Ternopil | Sokil-Orion | Debut | none |
| Volyn | Troyanda-Ekspres | 1 | Final |
Notes:
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.
| width=20% | width=12% | width=20% | ||||
|---|---|---|---|---|---|---|
| Korona Ivano-Frankivsk | 2:4 | Dynamo-Orbita Kamianets-Podilsky | 1:0 and 1:4 | |||
| Psyol Hadiach | 1:3 | Naftovyk-2 Okhtyrka | 1:1 and 0:2 | |||
| HPZ Varva | 2:0 | Krystal Parkhomivka | 2:0 and 0:0 | |||
| Ekina Almazna | 1:2 | Shakhta Ukraina Ukrainsk | 1:1 and 0:1 | |||
| Rochyn Sosnivka | +:- | Sokil-Orion Velyki Hayi |
| width=20% | width=12% | width=20% | ||||
|---|---|---|---|---|---|---|
| Chaika Vyshhorod | 2:4 | Troyanda-Ekspres Hirka Polonka | 1:0 and 1:4 | |||
| Dynamo-Orbita Kamianets-Podilsky | +:- | Rochyn Sosnivka | ||||
| Naftovyk-2 Okhtyrka | 3:3 | HPZ Varva | 2:2 and 1:1 | |||
| Shakhta Ukraina Ukrainsk | 6:4 | Signal Odesa | 2:1 and 4:3 |
| width=20% | width=12% | width=20% | ||||
|---|---|---|---|---|---|---|
| Dynamo-Orbita Kamianets-Podilsky | 3:5 | Troyanda-Ekspres Hirka Polonka | 3:3 and 0:2 | |||
| HPZ Varva | 1:2 | Shakhta Ukraina Ukrainsk | 1:0 and 0:2 |