Russian Cup 2022/23, 1/128 finals |
 | 31.08.2022 |  | Chernomorets (Novorossiysk) | – | Druzhba (Maykop) | | 2:0 (1:0) |
| Novorossiysk |
Russian Cup 2021/22, 1/256 finals |
| 18.07.2021 | | Forte (Taganrog) | – | Druzhba (Maykop) | | 3:0 (2:0) |
| Taganrog |
Russian Cup 2020/21, 1/128 finals |
| 19.08.2020 | | Biolog-Novokubansk (Novokubansk) | – | Druzhba (Maykop) | | 3:0 (1:0) |
| Progress |
Russian Cup 2019/20, 1/128 finals |
| 28.07.2019 | | Druzhba (Maykop) | – | Chernomorets (Novorossiysk) | | 0:1 aet
(0:0, 0:0) |
| Maykop |
Russian Cup 2018/19, 1/64 finals |
| 07.08.2018 | | Druzhba (Maykop) | – | Chernomorets (Novorossiysk) | | 0:1 (0:1) |
| Maykop |
Russian Cup 2017/18, 1/128 finals |
| 24.07.2017 | | Druzhba (Maykop) | – | Chernomorets (Novorossiysk) | | 2:4 (0:3) |
| Maykop |
Russian Cup 2016/17, 1/128 finals |
| 24.07.2016 | | Druzhba (Maykop) | – | Afips (Afipsky) | | 0:2 (0:1) |
| Maykop |
Russian Cup 2015/16, 1/256 finals |
| 15.07.2015 | | Druzhba (Maykop) | – | Biolog-Novokubansk (Novokubansk) | | 1:2 (1:1) |
| Maykop |
Russian Cup 2014/15, 1/64 finals |
| 16.08.2014 | | Druzhba (Maykop) | – | FK Astrahan (Astrakhan) | | 0:1 (0:0) |
| Maykop |
Russian Cup 2013/14, 1/256 finals |
| 07.07.2013 | | Dagdizel (Kaspiysk) | – | Druzhba (Maykop) | | 2:0 (1:0) |
| Derbent |
Russian Cup 2012/13, 1/128 finals |
| 05.08.2012 | | Alaniya (Vladikavkaz) reserve | – | Druzhba (Maykop) | | 4:0 (1:0) |
| Vladikavkaz |
Russian Cup 2011/12, 1/256 finals |
| 08.05.2011 | | Druzhba (Maykop) | – | Biolog (Novokubansk) | | 1:4 (0:1) |
| Maykop |
Russian Cup 2010/11, 1/256 finals |
| 26.04.2010 | | Chernomorets (Novorossiysk) | – | Druzhba (Maykop) | | 2:0 (1:0) |
| Novorossiysk |
Russian Cup 2009/10, 1/256 finals |
| 04.05.2009 | | FK Krasnodar-2000 (Krasnodar) | – | Druzhba (Maykop) | | 4:3 aet
(1:1, 3:3) |
| Krasnodar |
Russian Cup 2008/09, 1/256 finals |
| 04.05.2008 | | Druzhba (Maykop) | – | FK Taganrog (Taganrog) | | 2:3 (1:2) |
| Maykop |
Russian Cup 2007/08, 1/256 finals |
| 15.04.2007 | | Sochi-04 (Sochi) | – | Druzhba (Maykop) | | 2:1 (0:0) |
| Sochi |
Russian Cup 2005/06, 1/128 finals |
| 30.04.2005 | | Druzhba (Maykop) | – | Spartak-UGP (Anapa) | | 1:2 (1:2) |
| Maykop |
Russian Cup 2004/05, 1/256 finals |
| 13.04.2004 | | FK Krasnodar-2000 (Krasnodar) | – | Druzhba (Maykop) | | 1:0 aet
(0:0) |
| |
Russian Cup 2003/04, 1/256 finals |
| 14.04.2003 | | FK Krasnodar-2000 (Krasnodar) | – | Druzhba (Maykop) | | 5:0 (2:0) |
| |
Russian Cup 2002/03, 1/64 finals |
| 22.05.2002 | | Druzhba (Maykop) | – | FK Krasnodar-2000 (Krasnodar) | | 1:2 (1:1) |
| Maykop |
Russian Cup 2001/02, 1/256 finals |
| 24.03.2001 | | Druzhba (Maykop) | – | Zhemchuzhina (Sochi) | | 0:1 (0:1) |
| Khosta |
Russian Cup 2000/01, 1/512 finals |
| 29.03.2000 | | Venets (Gulkevichi) | – | Druzhba (Maykop) | | 4:0 (2:0) |
| Gulkevichi |
Russian Cup 1999/00, 1/32 finals |
| 28.06.1999 | | Sokol (Saratov) | – | Druzhba (Maykop) | | 8:1 (4:0) |
 | Saratov |
Russian Cup 1998/99, 1/16 finals |
| 12.09.1998 | | Druzhba (Maykop) | – | Rotor (Volgograd) | | 1:3 (1:1) |
| Maykop |
Russian Cup 1997/98, 1/32 finals |
| 06.07.1997 | | Dynamo (Stavropol) | – | Druzhba (Maykop) | | 5:3 (0:1) |
| Stavropol |
Russian Cup 1996/97, 1/16 finals |
| 03.08.1996 | | Druzhba (Maykop) | – | Rostselmash (Rostov-on-Don) | | 1:2 aet
(0:0, 1:1) |
| Maykop |
Russian Cup 1995/96, 1/64 finals |
| 16.05.1995 | | Avtodor-BMK (Vladikavkaz) | – | Druzhba (Maykop) | | 3:0 (2:0) |
| Vladikavkaz |
Russian Cup 1994/95, 1/64 finals |
| 27.06.1994 | | Spartak (Anapa) | – | Druzhba (Maykop) | | 3:1 aet
(0:1, 1:1) |
| Anapa |
Russian Cup 1993/94, 1/32 finals |
| 16.06.1993 | | Gekris (Novorossiysk) | – | Druzhba (Maykop) | | 4:1 (1:0) |
| Novorossiysk |
Russian Cup 1992/93, Semifinal |
| 27.05.1993 | | Torpedo (Moscow) | – | Druzhba (Maykop) | | 1:0 (1:0) |
| Moscow |
