Ukrainian Cup 2021/22, 1/16 finals |
 | 21.09.2021 |  | Metallist (Kharkiv) | – | Desna (Chernihiv) | | 2:1 (0:1) |
| Kharkiv |
Ukrainian Cup 2020/21, 1/8 finals |
| 16.12.2020 | | Desna (Chernihiv) | – | Zorya (Lugansk) | | 0:1 (0:1) * |
| Kiev |
Ukrainian Cup 2019/20, Quarterfinal |
| 12.03.2020 | | Desna (Chernihiv) | – | Vorskla (Poltava) | | 0:1 (0:0) * |
| Chernigiv |
Ukrainian Cup 2017/18, Quarterfinal |
| 29.11.2017 | | Desna (Chernihiv) | – | Dynamo (Kyiv) | | 0:2 (0:1) |
| Chernigiv |
Ukrainian Cup 2014/15, 1/16 finals |
| 23.08.2014 | | Desna (Chernihiv) | – | Dnipro (Dnipropetrovsk) | | 0:1 (0:1) |
 | Chernigiv |
Ukrainian Cup 2013/14, Quarterfinal |
| 26.03.2014 | | Desna (Chernihiv) | – | Shakhtar (Donetsk) | | 0:2 (0:0) |
| Chernigiv |
Ukrainian Cup 2012/13, 1/16 finals |
| 23.09.2012 | | Desna (Chernihiv) | – | Vorskla (Poltava) | | 1:2 (0:2) |
| Chernigiv |
Ukrainian Cup 2011/12, Second preliminary round |
| 17.08.2011 | | Desna (Chernihiv) | – | Enerhetyk (Burshtyn) | | 0:2 (0:1) |
| Chernigiv |
Ukrainian Cup 2010/11, First Preliminary Round |
| 28.07.2010 | | Desna (Chernihiv) | – | Enerhiya (Nova Kahovka) | | 1:2 (0:1) |
| Chernigiv |
Ukrainian Cup 2009/10, Second preliminary round |
| 05.08.2009 | | Desna (Chernihiv) | – | Nyva (Ternopol) | | 1:2 (0:2) |
| Chernigiv |
Ukrainian Cup 2008/09, 1/16 finals |
| 13.09.2008 | | Desna (Chernihiv) | – | FK Kharkiv (Kharkiv) | | 1:4 (0:1) |
| Chernigiv |
Ukrainian Cup 2006/07, 1/16 finals |
| 20.09.2006 | | Desna (Chernihiv) | – | FK Kharkiv (Kharkiv) | | 0:2 (0:2) |
| Chernigiv |
Ukrainian Cup 2005/06, 1/32 finals |
| 13.08.2005 | | Desna (Chernihiv) | – | Shakhtar (Donetsk) | | 2:5 (1:3) |
| Chernigiv |
Ukrainian Cup 2004/05, 1/8 finals |
| 12.09.2004 | | Desna (Chernihiv) | – | Kryvbas (Kryvyi Rih) | | 1:4 (1:4) |
| Chernigiv |
Ukrainian Cup 2003/04, 1/32 finals |
| 09.08.2003 | | Desna (Chernihiv) | – | Dnipro (Dnipropetrovsk) | | 0:2 (0:1) |
| Chernigiv |
Ukrainian Cup 2002/03, 1/32 finals |
| 10.08.2002 | | Desna (Chernihiv) | – | Stal (Alchevsk) | | 0:1 (0:0) |
| Chernigiv |
Ukrainian Cup 2001/02, First stage |
| 18.07.2001 | | Mashynobudivnyk (Druzhkivka) | – | Desna (Chernihiv) | | +:- |
| |
Ukrainian Cup 1999/00, First stage. Second League Cup, 1/16 finals |
| 22.09.1999 | | Dynamo-3 (Kyiv) | – | Desna (Chernihiv) | | 1:0 (1:0) |
| Kiev |
Ukrainian Cup 1999/00, First stage. Second League Cup, 1/16 finals |
| 01.09.1999 | | Desna (Chernihiv) | – | Dynamo-3 (Kyiv) | | 2:4 (1:1) |
| Chernigiv |
Ukrainian Cup 1998/99, 1/16 finals |
| 16.10.1998 | | Prikarpattya (Ivano-Frankivsk) | – | Desna (Chernihiv) | | 1:0 (0:0) |
| Ivano-Frankivsk |
Ukrainian Cup 1998/99, 1/32 finals |
| 02.10.1998 | | Hazovyk (Komarno) | – | Desna (Chernihiv) | | 2:0 (1:0) |
| Komarno Gazovyk Stadium |
Ukrainian Cup 1997/98, 1/16 finals |
| 26.10.1997 | | Metalurh (Mariupol) | – | Desna (Chernihiv) | | 5:3 (0:2) |
| Mariupol |
Ukrainian Cup 1997/98, 1/64 finals |
| 26.07.1997 | | Tsementnyk-Khorda (Mykolaiv) | – | Desna (Chernihiv) | | 4:1 aet
(2:0, 3:0) |
| Mykolaiv |
Ukrainian Cup 1996/97, 1/32 finals |
| 18.09.1996 | | Desna (Chernihiv) | – | Yavir (Krasnopillya) | | -:+ |
| |
Ukrainian Cup 1994/95, 1/32 finals |
| 05.09.1994 | | Systema-Boreks (Boyarka) | – | Desna (Chernihiv) | | 1:0 (0:0) |
| Borodyanka Systema SC |
Ukrainian Cup 1993/94, 1/16 finals |
| 03.11.1993 | | Torpedo (Zaporizhzhya) | – | Desna (Chernihiv) | | 4:2 (1:0) |
| Zaporizhia |
Ukrainian Cup 1992/93, 1/64 finals |
| 01.08.1992 | | Dynamo-3 (Kyiv) | – | Desna (Chernihiv) | | 2:0 (0:0) |
| Kiev |
Ukrainian Cup 1992, 1/32 finals |
| 16.02.1992 | | Vorskla (Poltava) | – | Desna (Chernihiv) | | 1:0 (0:0) |
| Poltava |
