18‑Nov‑2019 | M15 Austin TX | Hard | QF | 733 | 369 | Collin Altamirano [USA] d. (6)Habib | 6-3 6-1 | | | | | | | | | |
18‑Nov‑2019 | M15 Austin TX | Hard | R16 | 733 | 1599 | (6)Habib d. Demetris Azoides [GRE] | 6-4 6-3 | | | | | | | | | |
18‑Nov‑2019 | M15 Austin TX | Hard | R32 | 733 | 1108 | (6)Habib d. Aron Pierce [USA] | 6-3 6-3 | | | | | | | | | |
14‑Oct‑2019 | M25 Waco TX | Hard | QF | 727 | 431 | (2)Jordi Arconada [ARG] d. Habib | 6-2 6-3 | | | | | | | | | |
14‑Oct‑2019 | M25 Waco TX | Hard | R16 | 727 | 524 | Habib d. Simon Carr [IRL] | 7-6(5) 6-3 | | | | | | | | | |
14‑Oct‑2019 | M25 Waco TX | Hard | R32 | 727 | 495 | Habib d. Evan Zhu [USA] | 6-3 2-6 6-4 | | | | | | | | | |
13‑Sep‑2019 | Davis Cup G1 R1: UZB vs LBN | Clay | RR | 671 | 362 | Sanjar Fayziev [UZB] d. Habib | 6-4 6-4 | | | | | | | | | |
13‑Sep‑2019 | Davis Cup G1 R1: UZB vs LBN | Clay | RR | 671 | 873 | Djurabek Karimov [UZB] d. Habib | 6-4 1-6 6-1 | | | | | | | | | |
2‑Sep‑2019 | M25 La Marsa | Clay | R32 | 678 | 379 | Dragos Dima [ROU] d. Habib | 6-4 3-6 6-1 | | | | | | | | | |
5‑Aug‑2019 | M25 Edwardsville IL | Hard | R32 | 714 | 327 | Sekou Bangoura [USA] d. (IR )Habib | 6-4 6-3 | | | | | | | | | |
29‑Jul‑2019 | M25 Decatur IL | Hard | SF | | 509 | Jenson Brooksby [USA] d. Habib | 6-3 6-2 | | | | | | | | | |
29‑Jul‑2019 | M25 Decatur IL | Hard | QF | | 415 | Habib d. Skander Mansouri [TUN] | 6-4 6-2 | | | | | | | | | |
29‑Jul‑2019 | M25 Decatur IL | Hard | R16 | | 682 | Habib d. (6)Felix Corwin [USA] | 6-3 6-4 | | | | | | | | | |
29‑Jul‑2019 | M25 Decatur IL | Hard | R32 | | | Habib d. (WC)Preston Touliatos [USA] | 6-3 6-3 | | | | | | | | | |
22‑Jul‑2019 | M25 Champaign IL | Hard | R32 | | 278 | Liam Broady [GBR] d. (IR )Habib | 6-7(5) 6-1 6-4 | | | | | | | | | |
15‑Jul‑2019 | M25 Iowa City IA | Hard | QF | | 574 | (5)Aziz Dougaz [TUN] d. Habib | 6-4 6-2 | | | | | | | | | |
15‑Jul‑2019 | M25 Iowa City IA | Hard | R16 | | 380 | Habib d. Sekou Bangoura [USA] | 6-4 7-6(8) | | | | | | | | | |
15‑Jul‑2019 | M25 Iowa City IA | Hard | R32 | | | Habib d. (Q)Alexander Lebedev [USA] | 6-3 6-4 | | | | | | | | | |
10‑Jun‑2019 | M15 Cancun | Hard | F | | 557 | (2)Gerardo Lopez Villasenor [MEX] d. (7)Habib | 7-6(2) 6-4 | | | | | | | | | |
10‑Jun‑2019 | M15 Cancun | Hard | SF | | | (7)Habib d. (PR)Brandon Walkin [AUS] | 6-0 RET | | | | | | | | | |
10‑Jun‑2019 | M15 Cancun | Hard | QF | | | (7)Habib d. Connor Farren [USA] | 6-7(4) 6-2 6-4 | | | | | | | | | |
10‑Jun‑2019 | M15 Cancun | Hard | R16 | | | (7)Habib d. Errol Smith [USA] | 7-6(1) 6-4 | | | | | | | | | |
10‑Jun‑2019 | M15 Cancun | Hard | R32 | | | (7)Habib d. Alex Blumenberg [BRA] | 6-3 6-2 | | | | | | | | | |
3‑Jun‑2019 | M15 Cancun | Hard | QF | | | Adam El Mihdawy [USA] d. Habib | 6-3 6-2 | | | | | | | | | |
3‑Jun‑2019 | M15 Cancun | Hard | R16 | | 481 | Habib d. Lucas Gomez [MEX] | 7-6(6) 6-4 | | | | | | | | | |
3‑Jun‑2019 | M15 Cancun | Hard | R32 | | | Habib d. Alejandro Mendoza [BOL] | 6-2 6-3 | | | | | | | | | |