Russian Cup 2020/21, 1/256 finals |
 | 05.08.2020 | | Anzhi (Makhachkala) | – | FK Makhachkala (Makhachkala) | | 1:0 (1:0) * |
| Makhachkala |
Russian Cup 2018/19, 1/16 finals |
| 26.09.2018 | | Chaika (Peschanokopskoye) | – | Anzhi (Makhachkala) | | 1:2 (0:1) |
| Peschanokopskoye |
Russian Cup 2016/17, 1/8 finals |
| 27.10.2016 | | Anzhi (Makhachkala) | – | Zenit (Saint Petersburg) | | 4:0 (1:0) |
| Kaspiysk |
Russian Cup 2016/17, 1/16 finals |
| 21.09.2016 | | Mordovia (Saransk) | – | Anzhi (Makhachkala) | | 1:2 (0:2) |
| Saransk |
Russian Cup 2015/16, 1/16 finals |
| 23.09.2015 | | Sokol (Saratov) | – | Anzhi (Makhachkala) | | 2:4 (1:1) |
 | Saratov |
Russian Cup 2014/15, 1/32 finals |
| 30.08.2014 | | Chernomorets (Novorossiysk) | – | Anzhi (Makhachkala) | | 1:4 (0:2) |
| Novorossiysk |
Russian Cup 2012/13, Semifinal |
| 08.05.2013 | | Zenit (Saint Petersburg) | – | Anzhi (Makhachkala) | | 0:1 (0:0) |
| Saint Petersburg |
Russian Cup 2012/13, Quarterfinal |
| 17.04.2013 | | Anzhi (Makhachkala) | – | Dynamo (Moscow) | | 1:0 aet
(0:0) |
| Kaspiysk |
Russian Cup 2012/13, 1/8 finals |
| 31.10.2012 | | Anzhi (Makhachkala) | – | Krylia Sovetov (Samara) | | 2:1 (1:1) |
| Makhachkala |
Russian Cup 2011/12, 1/16 finals |
| 17.07.2011 | | Volga (Ulyanovsk) | – | Anzhi (Makhachkala) | | 0:3 (0:2) |
| Ulyanovsk |
Russian Cup 2010/11, 1/16 finals |
| 14.07.2010 | | Pskov-747 (Pskov) | – | Anzhi (Makhachkala) | | 1:2 (1:1) |
| Pskov |
Russian Cup 2008/09, 1/32 finals |
| 01.07.2008 | | Anzhi (Makhachkala) | – | Mashuk-KMV (Pyatigorsk) | | 3:0 (0:0) |
| Makhachkala |
Russian Cup 2006/07, 1/32 finals |
| 21.06.2006 | | Anzhi (Makhachkala) | – | Volgar-Gazprom (Astrakhan) | | 2:0 (0:0) |
| Kaspiysk |
Russian Cup 2003/04, 1/16 finals |
| 14.10.2003 | | Anzhi (Makhachkala) | – | Rotor (Volgograd) | | 3:1 (1:0) |
| Kaspiysk |
Russian Cup 2003/04, 1/32 finals |
| 24.08.2003 | | Anzhi (Makhachkala) | – | Sokol (Saratov) | | 2:0 (2:0) |
| Kaspiysk |
Russian Cup 2002/03, 1/8 finals |
| 02.03.2003 | | Anzhi (Makhachkala) | – | Lokomotiv (Moscow) | | 1:0 (0:0) |
| Makhachkala |
Russian Cup 2002/03, 1/16 finals |
| 14.09.2002 | | Kuban (Krasnodar) | – | Anzhi (Makhachkala) | | 1:2 (1:1) |
| Krasnodar |
Russian Cup 2000/01, Semifinal |
| 16.05.2001 | | Anzhi (Makhachkala) | – | Krylia Sovetov (Samara) | | 2:1 (0:0) |
| Makhachkala |
Russian Cup 2000/01, Quarterfinal |
| 11.04.2001 | | Anzhi (Makhachkala) | – | Torpedo (Moscow) | | 1:0 (0:0) |
| Makhachkala |
Russian Cup 2000/01, 1/8 finals |
| 28.10.2000 | | CSKA (Moscow) | – | Anzhi (Makhachkala) | | 1:3 (1:2) |
| Moscow |
Russian Cup 2000/01, 1/16 finals |
| 10.09.2000 | | Oazis (Yartsevo) | – | Anzhi (Makhachkala) | | 1:2 aet
(0:0, 1:1) |
| Yartsevo |
Russian Cup 1999/00, 1/8 finals |
| 13.11.1999 | | Anzhi (Makhachkala) | – | Gazovik-Gazprom (Izhevsk) | | 2:0 (2:0) |
| Makhachkala |
Russian Cup 1999/00, 1/16 finals |
| 12.10.1999 | | Anzhi (Makhachkala) | – | Torpedo (Moscow) | | 3:1 (0:1) |
| Makhachkala |
Russian Cup 1999/00, 1/32 finals |
| 28.06.1999 | | Anzhi (Makhachkala) | – | Avtodor (Vladikavkaz) | | 4:0 (2:0) |
| Makhachkala |
Russian Cup 1998/99, 1/64 finals |
| 06.07.1998 | | Volgar-Gazprom (Astrakhan) | – | Anzhi (Makhachkala) | | 1:2 (0:2) |
| Astrakhan |
Russian Cup 1998/99, 1/128 finals |
| 27.05.1998 | | Anzhi (Makhachkala) | – | Nart (Nartkala) | | 7:0 (1:0) |
| Makhachkala |
Russian Cup 1997/98, 1/64 finals |
| 16.06.1997 | | Anzhi (Makhachkala) | – | Rotor-2 (Mikhailovka) | | 4:2 (2:1) |
| Kaspiysk |
Russian Cup 1997/98, 1/128 finals |
| 15.05.1997 | | Dynamo-Imamat (Makhachkala) | – | Anzhi (Makhachkala) | | 0:4 (0:3) |
| Makhachkala |
Russian Cup 1996/97, 1/32 finals |
| 30.06.1996 | | Anzhi (Makhachkala) | – | Spartak (Nalchik) | | 8:0 (5:0) |
| Kaspiysk |
Russian Cup 1996/97, 1/64 finals |
| 01.06.1996 | | Kavkazkabel (Prokhladnyi) | – | Anzhi (Makhachkala) | | 0:2 (0:2) |
| Prokhladny |
Russian Cup 1996/97, 1/128 finals |
| 02.05.1996 | | Anzhi (Makhachkala) | – | Dynamo-Imamat (Makhachkala) | | 2:0 (1:0) |
| Kaspiysk |
Russian Cup 1996/97, 1/256 finals |
| 21.04.1996 | | FK Derbent (Derbent) | – | Anzhi (Makhachkala) | | 1:2 (0:2) |
| Derbent |
Russian Cup 1995/96, 1/8 finals |
| 04.11.1995 | | Zhemchuzhina (Sochi) | – | Anzhi (Makhachkala) | | 0:3 (0:2) |
| Sochi |
Russian Cup 1995/96, 1/16 finals |
| 04.10.1995 | | Anzhi (Makhachkala) | – | Spartak-Alaniya (Vladikavkaz) | | 2:1 aet
(0:0, 1:1) |
| Kaspiysk City Stadium |
Russian Cup 1995/96, 1/32 finals |
| 04.07.1995 | | Anzhi (Makhachkala) | – | Zvezda (Gorodishche) | | +:- |
| |
Russian Cup 1995/96, 1/64 finals |
| 15.05.1995 | | Anzhi (Makhachkala) | – | Uralan (Elista) | | +:- |
| |
Russian Cup 1995/96, 1/128 finals |
| 06.05.1995 | | Volgar-Gazprom (Astrakhan) | – | Anzhi (Makhachkala) | | 0:2 (0:1) |
| Astrakhan |
Russian Cup 1994/95, 1/32 finals |
| 26.08.1994 | | Anzhi (Makhachkala) | – | Uralan (Elista) | | 4:0 (3:0) |
| Mineralnye Vody Lokomotiv Stadium |
Russian Cup 1994/95, 1/64 finals |
| 27.06.1994 | | Anzhi (Makhachkala) | – | Iriston (Vladikavkaz) | | +:- |
| |
Russian Cup 1994/95, 1/128 finals |
| 29.05.1994 | | Anzhi (Makhachkala) | – | Argo (Kaspiysk) | | 3:0 (1:0) |
| Makhachkala |
Russian Cup 1994/95, 1/256 finals |
| 09.05.1994 | | Dynamo (Makhachkala) | – | Anzhi (Makhachkala) | | 1:2 aet
(1:0, 1:1) |
| Makhachkala |
Russian Cup 1992/93, 1/128 finals |
| 02.05.1992 | | Anzhi (Makhachkala) | – | Erzu (Groznyi) | | 2:0 (2:0) |
| Makhachkala |
Russian Cup 1992/93, 1/256 finals |
| 18.04.1992 | | Anzhi (Makhachkala) | – | Vainakh (Shali) | | 5:0 (2:0) |
| Makhachkala |
