Ukrainian Cup 2021/22, Second Preliminary round |
 | 18.08.2021 |  | FK Sumy (Sumy) | – | Metalurh (Zaporizhzhya) | | 0:1 (0:1) |
| Mykolaivka FC Victoria Stadium |
Ukrainian Cup 2018/19, Third Preliminary round |
| 25.09.2018 | | FK Sumy (Sumy) | – | Karpaty (Lviv) | | 0:3 (0:1) |
| Sumy |
Ukrainian Cup 2017/18, Second Preliminary round |
| 26.07.2017 | | Dnipro-1 (Dnipro) | – | FK Sumy (Sumy) | | 2:0 (1:0) |
| Dnipro |
Ukrainian Cup 2016/17, Second Preliminary round |
| 10.08.2016 | | FK Sumy (Sumy) | – | Illichovets (Mariupol) | | 0:1 aet
(0:0, 0:0) |
| Sumy |
Ukrainian Cup 2015/16, 1/16 finals |
| 22.08.2015 | | FK Sumy (Sumy) | – | Obolon-Brovar (Kyiv) | | 0:1 (0:0) |
| Sumy |
Ukrainian Cup 2014/15, 1/16 finals |
| 24.08.2014 | | FK Sumy (Sumy) | – | Metalist (Kharkiv) | | 0:1 aet
(0:0) |
| Sumy |
Ukrainian Cup 2013/14, Second preliminary round |
| 07.08.2013 | | FK Sumy (Sumy) | – | Bukovyna (Chernivtsy) | | 0:1 (0:0) |
| Sumy |
Ukrainian Cup 2012/13, Second preliminary round |
| 22.08.2012 | | Avanhard (Kramatorsk) | – | FK Sumy (Sumy) | | 1:0 (0:0) |
| Kramatorsk |
Ukrainian Cup 2011/12, Round of 16 |
| 26.10.2011 | | FK Sumy (Sumy) | – | Zorya (Lugansk) | | 1:3 (1:1) |
| Sumy |
Ukrainian Cup 2010/11, First Preliminary Round |
| 27.07.2010 | | Skala (Morshin) | – | FK Sumy (Sumy) | | 3:2 (1:0) |
| Stryi |
Ukrainian Cup 2009/10, Second preliminary round |
| 05.08.2009 | | FK Sumy (Sumy) | – | Naftovyk-Ukrnafta (Okhtyrka) | | 0:1 (0:0) |
| Sumy |
Ukrainian Cup 2008/09, First Preliminary Round |
| 16.07.2008 | | Zirka (Kirovohrad) | – | Yavir (Krasnopillya) | | 1:0 (1:0) |
| Kirovograd |
Ukrainian Cup 2006/07, 1/16 finals |
| 20.09.2006 | | Yavir (Krasnopillya) | – | Shakhtar (Donetsk) | | 1:6 (0:4) |
| Sumy |
Ukrainian Cup 2005/06, 1/32 finals |
| 13.08.2005 | | Yavir (Krasnopillya) | – | Hazovyk-Skala (Stryi) | | 0:3 (0:0) |
| Krasnopillya Kolos Stadium |
Ukrainian Cup 2004/05, 1/16 finals |
| 20.08.2004 | | Yavir (Krasnopillya) | – | Dynamo (Kyiv) | | 0:6 (0:4) |
| Sumy |
Ukrainian Cup 2003/04, 1/32 finals |
| 09.08.2003 | | Yavir (Krasnopillya) | – | Shakhtar (Donetsk) | | 0:3 (0:1) |
| Krasnopillya Kolos Stadium |
Ukrainian Cup 2002/03, 1/8 finals |
| 19.10.2002 | | Yavir (Krasnopillya) | – | Dnipro (Dnipropetrovsk) | | 0:3 (0:2) |
| Krasnopillya Kolos Stadium |
