Russian Cup 2021/22, 1/64 finals |
 | 12.08.2021 |  | Legion-Dynamo (Makhachkala) | – | Anzhi (Makhachkala) | | 2:0 (1:0) |
| Makhachkala |
Russian Cup 2020/21, 1/128 finals |
| 19.08.2020 | | Legion-Dynamo (Makhachkala) | – | Anzhi (Makhachkala) | | 1:0 (0:0) |
| Makhachkala |
Russian Cup 2019/20, 1/128 finals |
| 28.07.2019 | | Alaniya (Vladikavkaz) | – | Anzhi (Makhachkala) | | 1:0 (0:0) |
| Vladikavkaz |
Russian Cup 2018/19, 1/8 finals |
| 01.11.2018 | | Spartak (Moscow) | – | Anzhi (Makhachkala) | | 1:0 (1:0) |
| Moscow |
Russian Cup 2017/18, 1/16 finals |
| 20.09.2017 | | Luch-Energiya (Vladivostok) | – | Anzhi (Makhachkala) | | 2:0 (1:0) |
| Vladivostok |
Russian Cup 2016/17, Quarterfinal |
| 01.03.2017 | | FK Ufa (Ufa) | – | Anzhi (Makhachkala) | | 1:0 (0:0) |
| Ufa |
Russian Cup 2015/16, 1/8 finals |
| 29.10.2015 | | FK Krasnodar (Krasnodar) | – | Anzhi (Makhachkala) | | 3:1 (2:0) |
| Krasnodar |
Russian Cup 2014/15, 1/16 finals |
| 24.09.2014 | | Anzhi (Makhachkala) | – | Zenit (Saint Petersburg) | | 1:2 (1:1) |
 | Kaspiysk |
Russian Cup 2013/14, 1/16 finals |
| 31.10.2013 | | Alaniya (Vladikavkaz) | – | Anzhi (Makhachkala) | | 1:0 (0:0) |
| Vladikavkaz |
Russian Cup 2011/12, 1/8 finals |
| 21.09.2011 | | Dynamo (Moscow) | – | Anzhi (Makhachkala) | | 1:0 aet
(0:0) |
| Khimki |
Russian Cup 2010/11, 1/8 finals |
| 01.03.2011 | | Anzhi (Makhachkala) | – | Zenit (Saint Petersburg) | | 2:3 (1:1) |
| Grozny |
Russian Cup 2009/10, 1/32 finals |
| 01.07.2009 | | Alaniya (Vladikavkaz) | – | Anzhi (Makhachkala) | | 3:0 (1:0) |
| Vladikavkaz |
Russian Cup 2008/09, 1/16 finals |
| 06.08.2008 | | Anzhi (Makhachkala) | – | Terek (Groznyi) | | 2:3 (2:3) |
| Makhachkala |
Russian Cup 2007/08, 1/32 finals |
| 13.06.2007 | | Rotor (Volgograd) | – | Anzhi (Makhachkala) | | 2:1 (0:1) |
| Volgograd |
Russian Cup 2006/07, 1/16 finals |
| 02.07.2006 | | Lokomotiv (Moscow) | – | Anzhi (Makhachkala) | | 4:2 (3:1) |
| Moscow |
Russian Cup 2005/06, 1/32 finals |
| 22.06.2005 | | Volgar-Gazprom (Astrakhan) | – | Anzhi (Makhachkala) | | 2:0 (2:0) |
| Astrakhan |
Russian Cup 2004/05, 1/32 finals |
| 02.07.2004 | | Olimpiya (Volgograd) | – | Anzhi (Makhachkala) | | 3:1 (1:1) |
| |
Russian Cup 2003/04, 1/16 finals |
| 05.11.2003 | | Rotor (Volgograd) | – | Anzhi (Makhachkala) | | 2:0 (0:0) |
| Volgograd |
Russian Cup 2002/03, Semifinal |
| 21.05.2003 | | Anzhi (Makhachkala) | – | FK Rostov (Rostov-on-Don) | | 0:1 (0:0) |
| Makhachkala |
Russian Cup 2001/02, 1/8 finals |
| 13.10.2001 | | Dynamo (Moscow) | – | Anzhi (Makhachkala) | | 5:0 (2:0) |
| Moscow |
Russian Cup 1998/99, 1/32 finals |
| 22.07.1998 | | Avtodor (Vladikavkaz) | – | Anzhi (Makhachkala) | | 3:1 (0:1) |
| Vladikavkaz |
Russian Cup 1997/98, 1/32 finals |
| 06.07.1997 | | Uralan (Elista) | – | Anzhi (Makhachkala) | | 2:0 (0:0) |
| Elista |
Russian Cup 1996/97, 1/16 finals |
| 14.08.1996 | | Anzhi (Makhachkala) | – | Alaniya (Vladikavkaz) | | 0:2 (0:1) |
| Makhachkala |
Russian Cup 1995/96, Quarterfinal |
| 11.04.1996 | | Dynamo (Moscow) | – | Anzhi (Makhachkala) | | 2:1 (0:0) |
| Moscow |
Russian Cup 1994/95, 1/16 finals |
| 05.10.1994 | | Anzhi (Makhachkala) | – | Spartak (Vladikavkaz) | | 1:2 (1:0) |
| Makhachkala |
Russian Cup 1993/94, 1/128 finals |
| 18.04.1993 | | Kavkazkabel (Prokhladnyi) | – | Anzhi (Makhachkala) | | 3:0 (2:0) |
| Prokhladny |
Russian Cup 1992/93, 1/64 finals |
| 13.06.1992 | | Terek (Groznyi) | – | Anzhi (Makhachkala) | | 5:3 (4:0) |
| Grozny |
