Ukrainian Cup 2023/24, 1/16 finals |
 | 23.08.2023 | | Zvyahel (Zvyahel) | – | Obolon (Kyiv) | | 0:1 (0:0) * |
| Zviahel |
Ukrainian Cup 2012/13, 1/16 finals |
| 23.09.2012 | | Obolon (Kyiv) | – | Metalist (Kharkiv) | | 1:4 (0:2) |
| Kiev |
Ukrainian Cup 2012/13, Second preliminary round |
| 22.08.2012 | | Obolon (Kyiv) | – | Arsenal (Bila Tserkva) | | 2:0 (1:0) |
| Kiev |
Ukrainian Cup 2011/12, 1/16 finals |
| 21.09.2011 | | Bukovyna (Chernivtsy) | – | Obolon (Kyiv) | | 2:1 (1:0) |
| Chernivtsi |
Ukrainian Cup 2010/11, 1/16 finals |
| 22.09.2010 | | FK Poltava (Poltava) | – | Obolon (Kyiv) | | 2:1 aet
(0:0, 1:1) |
| Poltava |
Ukrainian Cup 2009/10, Quarterfinal |
| 28.10.2009 | | Tavriya (Simferopil) | – | Obolon (Kyiv) | | 4:0 (3:0) |
| Simferopol |
Ukrainian Cup 2009/10, 1/8 finals |
| 12.09.2009 | | Stal (Alchevsk) | – | Obolon (Kyiv) | | 0:3 (0:2) |
 | Alchevsk |
Ukrainian Cup 2009/10, 1/16 finals |
| 15.08.2009 | | CSKA (Kyiv) | – | Obolon (Kyiv) | | 3:3 aet
(0:1, 2:4),
pen. 2:4 |
| Chapayevka |
Ukrainian Cup 2008/09, 1/8 finals |
| 28.10.2008 | | Obolon (Kyiv) | – | Vorskla (Poltava) | | 1:4 (1:1) |
| Kiev |
Ukrainian Cup 2008/09, 1/16 finals |
| 14.09.2008 | | Obolon (Kyiv) | – | Chornomorets (Odesa) | | 1:0 aet
(0:0) |
| Kiev |
Ukrainian Cup 2008/09, Second preliminary round |
| 06.08.2008 | | Obolon (Kyiv) | – | Naftovyk-Ukrnafta (Okhtyrka) | | 3:1 (2:1) |
| Kiev |
Ukrainian Cup 2007/08, Second preliminary round |
| 08.08.2007 | | Dynamo (Simferopol) | – | Obolon (Kyiv) | | 3:1 (2:1) |
| Simferopol |
Ukrainian Cup 2006/07, 1/16 finals |
| 20.09.2006 | | Obolon (Kyiv) | – | Stal (Alchevsk) | | 0:1 (0:1) |
| Kiev |
Ukrainian Cup 2006/07, 1/32 finals |
| 11.08.2006 | | Fakel (Ivano-Frankivsk) | – | Obolon (Kyiv) | | 0:1 (0:0) |
| Ivano-Frankivsk |
Ukrainian Cup 2005/06, 1/32 finals |
| 13.08.2005 | | Dnipro (Cherkasy) | – | Obolon (Kyiv) | | 0:0 aet,
pen. 4:2 |
| Cherkasy |
Ukrainian Cup 2004/05, 1/16 finals |
| 22.08.2004 | | CSKA (Kyiv) | – | Obolon (Kyiv) | | 2:2 aet
(1:0, 1:1),
pen. 6:5 |
| Kiev |
Ukrainian Cup 2004/05, 1/32 finals |
| 07.08.2004 | | Ros (Bila Tserkva) | – | Obolon (Kyiv) | | 0:1 (0:1) |
| Bila Tserkva |
Ukrainian Cup 2003/04, 1/8 finals |
| 29.10.2003 | | Stal (Alchevsk) | – | Obolon (Kyiv) | | 3:0 (1:0) |
| Alchevsk |
Ukrainian Cup 2003/04, 1/16 finals |
| 24.08.2003 | | Zorya (Lugansk) | – | Obolon (Kyiv) | | 2:5 (1:1) |
| Lugansk |
Ukrainian Cup 2003/04, 1/32 finals |
| 10.08.2003 | | Naftovyk (Dolyna) | – | Obolon (Kyiv) | | 0:1 (0:1) |
| Dolyna |
Ukrainian Cup 2002/03, 1/8 finals |
| 19.10.2002 | | Obolon (Kyiv) | – | Metalurh (Donetsk) | | 0:1 (0:0) |
| Kiev |
Ukrainian Cup 2002/03, 1/16 finals |
| 24.08.2002 | | Spartak (Sumy) | – | Obolon (Kyiv) | | 0:2 (0:1) |
| Sumy |
Ukrainian Cup 2002/03, 1/32 finals |
| 10.08.2002 | | Lukor (Kalush) | – | Obolon (Kyiv) | | 1:4 (1:2) |
| Kalush |
Ukrainian Cup 2001/02, 1/8 finals |
| 27.10.2001 | | Dynamo (Kyiv) | – | Obolon (Kyiv) | | 3:0 (0:0) |
| Kiev |
Ukrainian Cup 2001/02, 1/8 finals |
| 20.10.2001 | | Obolon (Kyiv) | – | Dynamo (Kyiv) | | 0:3 (0:0) |
| Kiev |
Ukrainian Cup 2001/02, 1/16 finals |
| 14.10.2001 | | Obolon (Kyiv) | – | Nyva (Ternopol) | | 2:0 (0:0) |
| Shchastlive UPK Stadium |
Ukrainian Cup 2001/02, 1/16 finals |
| 04.10.2001 | | Nyva (Ternopol) | – | Obolon (Kyiv) | | 0:1 (0:1) |
| Ternopil |
Ukrainian Cup 2001/02, Fourth stage |
| 16.09.2001 | | Obolon (Kyiv) | – | SK Mykolaiv (Mykolaiv) | | 4:2 (0:1) |
| Shchastlive UPK Stadium |
Ukrainian Cup 2001/02, Fourth stage |
| 07.09.2001 | | SK Mykolaiv (Mykolaiv) | – | Obolon (Kyiv) | | 0:1 (0:1) |
| Mykolaiv |
Ukrainian Cup 2000/01, First stage. Second League Cup, quarterfinal |
| 30.08.2000 | | Polissya (Zhytomyr) | – | Obolon-PVO (Kyiv) | | 4:0 (1:0) |
| Zhytomyr |
Ukrainian Cup 2000/01, First stage. Second League Cup, 1/8 finals |
| 16.08.2000 | | Obolon-PVO (Kyiv) | – | Adoms (Kremenchuk) | | 2:0 (1:0) |
| Brovary |
Ukrainian Cup 2000/01, First stage. Second League Cup, 1/16 finals |
| 06.08.2000 | | Desna (Chernihiv) | – | Obolon-PVO (Kyiv) | | 1:1 aet
(0:0, 1:1),
pen. 5:6 |
| Chernigiv |
Ukrainian Cup 1999/00, 1/16 finals |
| 11.03.2000 | | Obolon-PVO (Kyiv) | – | Nyva (Ternopol) | | 0:1 (0:1) |
| Nova Kakhovka |
Ukrainian Cup 1998/99, 1/64 finals |
| 27.09.1998 | | Obolon-PVO (Kyiv) | – | Yavir (Krasnopillya) | | 1:2 (0:1) |
| Kiev Bilshovyk Stadium |
Ukrainian Cup 1998/99, 1/64 finals |
| 22.09.1998 | | Yavir (Krasnopillya) | – | Obolon-PVO (Kyiv) | | 2:1 (1:1) |
| Krasnopillya Kolos Stadium |
Ukrainian Cup 1998/99, 1/128 finals |
| 29.08.1998 | | Obolon-PVO (Kyiv) | – | Hirnyk-Sport (Komsomolsk) | | 3:1 (1:1) |
| Kiev Bilshovyk Stadium |
Ukrainian Cup 1998/99, 1/128 finals |
| 25.08.1998 | | Hirnyk-Sport (Komsomolsk) | – | Obolon-PVO (Kyiv) | | 0:2 (0:0) |
| Komsomolsk |
Ukrainian Cup 1997/98, 1/128 finals |
| 18.07.1997 | | Dynamo-3 (Kyiv) | – | Obolon-PVO (Kyiv) | | 3:1 (0:1) |
| Kiev |
Ukrainian Cup 1996/97, 1/32 finals |
| 18.09.1996 | | Obolon (Kyiv) | – | Dynamo-2 (Kyiv) | | 1:2 (1:0) |
| Kiev |
Ukrainian Cup 1996/97, 1/64 finals |
| 28.08.1996 | | Obolon (Kyiv) | – | Dnipro (Cherkasy) | | 3:0 (2:0) |
| Kiev |
Ukrainian Cup 1995/96, 1/64 finals |
| 16.10.1995 | | Obolon (Kyiv) | – | Hazovyk (Komarno) | | 0:2 (0:1) |
| Kiev Bilshovyk Stadium |
Ukrainian Cup 1995/96, 1/128 finals |
| 01.08.1995 | | EKO-Servis (Rivne) | – | Obolon (Kyiv) | | 0:1 aet
(0:0) |
| Rivne |
Ukrainian Cup 1994/95, 1/64 finals |
| 01.09.1994 | | Obolon-Zmina (Kyiv) | – | Borisfen (Borispil) | | 1:3 (1:1) |
| Kiev |
Ukrainian Cup 1994/95, 1/128 finals |
| 21.08.1994 | | Obolon-Zmina (Kyiv) | – | Sula (Lubny) | | 3:0 (2:0) |
| Kiev |
