The 1939 Ukrainian Cup was a football knockout competition conducting by the Football Federation of the Ukrainian SSR and was known as the Ukrainian Cup.
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| Lokomotyv Lozova | 1:5 | Stal Dniprodzerzhynsk | ||||
| Stal Mariupol | 2:1 | Zenit Stalino | ||||
| Avanhard Kramatorsk | 3:0 | Lokomotyv imeni Kahanovycha | ||||
| Dynamo Vinnytsia | -/+ | Dynamo Kamianets-Podilskyi | ||||
| Traktor Kharkiv | 2:0 | Stal Kostiantynivka | ||||
| Lokomotyv zavodiv Zaporizhia | 1:2 | Blyskavka Kharkiv | ||||
| Lokomotyv Pivdnia Voznesensk | +/- | Spartak Tiraspol | ||||
| Spartak Chernihiv | 2:3 | Lokomotyv Kyiv | ||||
| Khachovyk Odesa | 4:3 | Rot-Front Kyiv | ||||
| Silmash Kirovohrad | 1:2 | Rot-Front Smila | ||||
| Stakhanovets Ordzhonikidze | 2:1 | Lokomotyv Pivdnia Dnipropetrovsk | ||||
| Avanhard Druzhkivka | 2:4 | Lokomotyv Pivdnia Kharkiv | ||||
| Avanhard Berdychiv | 2:6 | Snaiper Odesa | ||||
| Stal Dnipropetrovsk | 2:1 | Zenit Kharkiv | ||||
| Dynamo Kremenchuk | 0:4 | Sudnobudivnyk Mykolaiv | ||||
| Tsukrovyk Sumy | 1:0 | Dynamo-2 Kyiv |
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| Stal Dniprodzerzhynsk | 4:2 | Stal Mariupol | ||||
| Avanhard Kramatorsk | 9:0 | Dynamo Kamianets-Podilskyi | ||||
| Traktor Kharkiv | 3:1 | Blyskavka Kharkiv | ||||
| Lokomotyv Pivdnia Voznesensk | 4:3 | Lokomotyv Kyiv | ||||
| Rot-Front Smila | 2:0 | Kharchovyk Odesa | ||||
| Stakhanovets Ordzhonikidze | 4:2 | Lokomotyv Pivdnia Kharkiv | ||||
| Snaiper Odesa | 3:2 | Stal Dnipropetrovsk | ||||
| Sudnobudivnyk Mykolaiv | 4:0 | Tsukrovyk Sumy |
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|---|---|---|---|---|---|---|
| Stal Dniprodzerzhynsk | 1:2 | Avanhard Kramatorsk | 3:2, 2:2 | |||
| Traktor Kharkiv | 3:0 | Lokomotyv Pivdnia Voznesensk | ||||
| Kharchovyk Odesa | 4:0 | Stakhanovets Ordzhonikidze | 0:0 | |||
| Snaiper Odesa | 2:0 | Sudnobudivnyk Mykolaiv |
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|---|---|---|---|---|---|---|
| Avanhard Kramatorsk | 2:1 | Traktor Kharkiv | ||||
| Kharchovyk Odesa | 3:1 | Snaiper Odesa | 1:1 |