The draw of the qualifying and preliminary rounds was held on 7 May 2019. The matches were played between 8 and 25 May 2019.
Dushanbe and Rasht zones
First qualifying round
8 May: “Rasht” - “Mehrgon” - 4: 1
Second qualifying round
11 May : “Orzu” - “Rasht” - 6: 0 15 May : “Rasht” - “Orzu” - 2: 0
Third qualifying round
19 May : “Orzu” - “Zarafshon” - 0: 1 25 May : “Zarafshon” - “Orzu” - 3: 1
Khatlon zone
First qualifying round
8 May : Kushoniyon - Mohir - 0: 1 11 May : “Mohir” - “Kushoniyon” - 6: 3
Preliminary round
The first legs were played on 26–28 May 2019, and the second legs were played on 8–9 and 18 June 2019. 26 May : “Ravshan” - “Dusti” - 1: 3 26 May : “Isfara” - “Ravshan” - 2: 0 27 May : “Barkchi” - “Shohmansur” - 4: 1 27 May : Vahdat - Lokomotiv-Pamir - 0: 0 27 May : “Khulbuk” - “Faizkand” - 3: 2 27 May : “Saroykamar” - “Mohir” - 5: 2 27 May : “Eskhata” - “Parvoz” - 0: 1 28 May : Dushanbe-83 - Zarafshon - 3: 0 8 June : “Shohmansur” - “Barkchi” - 0: 6 8 June : “Faizkand” - “Khulbuk” - 0: 0 8 June : “Parvoz” - “Eskhata” - 1: 2 9 June : “Dusti” - “Ravshan” - 2: 1 9 June : “Mohir” - “Saroykamar” - 1: 3 9 June : Ravshan - Isfara - 0: 0 18 June : “Lokomotiv-Pamir” - “Vahdat” - 0: 1 Not played : Zarafshon - Dushanbe-83 - 0: 3
Round of 16
The draw for the round of 16 onwards was held on 12 July 2019. Teams from the Tajikistan Higher League entered at this stage. The first legs were played on 30–31 July and 2 August 2019, and the second legs were played on 3–6 August 2019. 30 July : “Saroykamar” - “Khatlon” - 0: 1 30 July : “Khujand” - “Vahdat” - 7: 0 30 July : "Dushanbe-83" - CSKA "Pamir" - 1: 1 31 July : Regar-TadAZ - Kuktosh - 0: 0 31 July : “Eskhata” - “Isfara” - 4: 2 31 July : “Istaravshan” - “Khulbuk” - 1: 0 31 July : “Dusti” - “Panjsher” - 1: 1 2 August : Istiklol - Barkchi - 7: 2 3 August : “Khatlon” - “Saroykamar” - 5: 1 3 August : CSKA Pamir - Dushanbe-83 - 0: 0 3 August : “Isfara” - “Eskhata” - 3: 3 4 August : “Kuktosh” - “Regar-TadAZ” - 2: 2 4 August : “Khulbuk” - “Istaravshan” - 3: 1 4 August : Panjshir - Dusti - 0: 1 5 August : Barkchi - Istiklol - 1: 7 6 August : “Vahdat” - “Khujand” - 0: 5
Quarter-finals
The first legs were played on 21 August 2019, and the second legs were played on 27 August 2019. 21 August : “Khatlon” - “Khujand” - 0: 2 21 August : “Eskhata” - “Istiklol” - 1: 2 21 August : CSKA Pamir - Regar-TadAZ - 1: 1 21 August : “Hulbuk” - “Dusti” - 2: 1 27 August : “Khujand” - “Khatlon” - 1: 0 27 August : "Regar-TadAZ" - CSKA "Pamir" - 2: 1 27 August : “Dusti” - “Hulbuk” - 2: 2 27 August : “Istiklol” - “Eskhata” - 6: 0
Semi-finals
The first legs were played on 1 October 2019, and the second legs were played on 1 November 2019.
