Ukrainian Cup 2021/22, Third Preliminary round |
 | 31.08.2021 | | LNZ (Cherkasy) | – | Olympic (Donetsk) | | 2:1 (0:0) |
| Cherkasy |
Ukrainian Cup 2021/22, Second Preliminary round |
| 18.08.2021 | | Livyi Bereh (Kyiv) | – | Olympic (Donetsk) | | 2:3 (1:2) |
| Kiev |
Ukrainian Cup 2020/21, Third Preliminary round |
| 13.11.2020 | | VPK-Ahro (Mahdalynivka) | – | Olympic (Donetsk) | | 1:0 (0:0) |
| Dnipro |
Ukrainian Cup 2019/20, 1/8 finals |
| 30.10.2019 | | FK Mariupol (Mariupol) | – | Olympic (Donetsk) | | 1:0 (0:0) |
| Mariupol |
Ukrainian Cup 2019/20, Third Preliminary round |
| 25.09.2019 | | Kremin (Kremenchuk) | – | Olympic (Donetsk) | | 2:3 (1:2) |
| Poltava |
Ukrainian Cup 2018/19, 1/8 finals |
| 31.10.2018 | | Shakhtar (Donetsk) | – | Olympic (Donetsk) | | 3:2 (0:0) |
| Kharkiv |
Ukrainian Cup 2018/19, Third Preliminary round |
| 26.09.2018 | | Zirka (Kropyvnytskyi) | – | Olympic (Donetsk) | | 1:1 aet
(0:1, 1:1),
pen. 4:5 |
| Kropyvnytskyi |
Ukrainian Cup 2017/18, 1/8 finals |
| 25.10.2017 | | Vorskla (Poltava) | – | Olympic (Donetsk) | | 2:0 aet
(0:0, 0:0) |
| Poltava |
Ukrainian Cup 2016/17, 1/16 finals |
| 21.09.2016 | | Volyn (Lutsk) | – | Olympic (Donetsk) | | 2:1 (0:0) |
| Lutsk |
Ukrainian Cup 2015/16, 1/8 finals |
| 28.10.2015 | | Dnipro (Dnipropetrovsk) | – | Olympic (Donetsk) | | 3:2 (1:0) |
 | Dnipropetrovsk |
Ukrainian Cup 2015/16, 1/8 finals |
| 23.09.2015 | | Olympic (Donetsk) | – | Dnipro (Dnipropetrovsk) | | 0:2 (0:1) |
| Kiev |
Ukrainian Cup 2015/16, 1/16 finals |
| 22.08.2015 | | Naftovyk-Ukrnafta (Okhtyrka) | – | Olympic (Donetsk) | | 0:2 (0:1) |
| Okhtyrka |
Ukrainian Cup 2014/15, Semifinal |
| 20.05.2015 | | Dynamo (Kyiv) | – | Olympic (Donetsk) | | 4:1 (2:0) |
| Kiev |
Ukrainian Cup 2014/15, Semifinal |
| 29.04.2015 | | Olympic (Donetsk) | – | Dynamo (Kyiv) | | 0:0 |
| Kiev |
Ukrainian Cup 2014/15, Quarterfinal |
| 08.04.2015 | | Olympic (Donetsk) | – | Vorskla (Poltava) | | 1:0 (0:0) |
| Kiev |
Ukrainian Cup 2014/15, Quarterfinal |
| 04.03.2015 | | Vorskla (Poltava) | – | Olympic (Donetsk) | | 0:0 |
| Poltava |
Ukrainian Cup 2014/15, Round of 16 |
| 28.10.2014 | | Metalurh (Zaporizhzhya) | – | Olympic (Donetsk) | | 0:4 (0:3) |
| Zaporizhia |
Ukrainian Cup 2014/15, Round of 16 |
| 28.09.2014 | | Olympic (Donetsk) | – | Metalurh (Zaporizhzhya) | | 2:0 (1:0) |
| Kiev |
Ukrainian Cup 2014/15, 1/16 finals |
| 23.08.2014 | | Real Pharma (Ovidiopol) | – | Olympic (Donetsk) | | 0:1 (0:1) |
| Odesa |
Ukrainian Cup 2013/14, Second preliminary round |
| 07.08.2013 | | Olympic (Donetsk) | – | PFK Oleksandriya (Oleksandriya) | | 0:0 aet,
pen. 2:5 |
| Donetsk |
Ukrainian Cup 2012/13, Second preliminary round |
| 22.08.2012 | | Helios (Kharkiv) | – | Olympic (Donetsk) | | 3:0 (1:0) |
| Kharkiv |
Ukrainian Cup 2011/12, Second preliminary round |
| 16.08.2011 | | Bukovyna (Chernivtsy) | – | Olympic (Donetsk) | | 3:2 (1:0) |
| Chernivtsi |
Ukrainian Cup 2010/11, Second preliminary round |
| 18.08.2010 | | Olympic (Donetsk) | – | Arsenal (Bila Tserkva) | | 1:3 (0:1) |
| Donetsk |
Ukrainian Cup 2009/10, First Preliminary Round |
| 18.07.2009 | | Morshin (Morshin) | – | Olympic (Donetsk) | | +:- |
| Stryi |
Ukrainian Cup 2008/09, Second preliminary round |
| 04.08.2008 | | Olympic (Donetsk) | – | Zirka (Kirovohrad) | | 0:4 (0:0) |
| Donetsk |
Ukrainian Cup 2008/09, First Preliminary Round |
| 16.07.2008 | | Olympic (Donetsk) | – | Hirnyk (Kryvyi Rih) | | 4:1 (1:1) |
| Donetsk |
Ukrainian Cup 2007/08, 1/16 finals |
| 26.09.2007 | | Olympic (Donetsk) | – | Desna (Chernihiv) | | 1:2 (0:0) |
| Donetsk |
Ukrainian Cup 2007/08, Second preliminary round |
| 08.08.2007 | | Olympic (Donetsk) | – | Hirnyk-Sport (Komsomolsk) | | 2:1 aet
(1:0, 1:1) |
| Donetsk |
Ukrainian Cup 2007/08, First Preliminary Round |
| 20.07.2007 | | Olympic (Donetsk) | – | Shakhtar (Sverdlovsk) | | 3:2 aet
(1:1, 2:2) |
| Donetsk |
Ukrainian Cup 2006/07, 1/16 finals |
| 20.09.2006 | | Olympic (Donetsk) | – | Kryvbas (Kryvyi Rih) | | 1:2 (0:0) |
| Donetsk |
Ukrainian Cup 2006/07, 1/32 finals |
| 11.08.2006 | | Olympic (Donetsk) | – | Podillya (Khmelnytskyi) | | 4:2 aet
(1:1, 2:2) |
| Donetsk |
Ukrainian Cup 2005/06, 1/32 finals |
| 13.08.2005 | | Olympic (Donetsk) | – | Krymteplytsya (Molodizhne) | | 2:3 (1:2) |
| Donetsk |
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