| 22‑Jul‑2019 | M25 Champaign IL | Hard | R16 | 380 | | Aleksandar Kovacevic [USA] d. (2)Hiltzik | 2-6 6-2 6-1 | | | | | | | | | |
| 22‑Jul‑2019 | M25 Champaign IL | Hard | R32 | 380 | | (2)Hiltzik d. Preston Touliatos [USA] | 7-6(6) 6-7(4) 6-3 | | | | | | | | | |
| 8‑Jul‑2019 | Winnetka CH | Hard | R32 | 387 | 193 | (14)Christopher Eubanks [USA] d. Hiltzik | 6-3 6-3 | | 0.66 | 3.4% | 1.7% | 50.8% | 53.3% | 41.4% | 7/12 | 0:58 |
| 8‑Jul‑2019 | Winnetka CH | Hard | R64 | 387 | 229 | Hiltzik d. Tim Smyczek [USA] | 6-2 3-6 6-3 | | 1.24 | 11.1% | 4.2% | 59.7% | 81.4% | 44.8% | 2/4 | 1:30 |
| 10‑Jun‑2019 | Columbus CH | Hard | R64 | 383 | 333 | Evan Song [USA] d. Hiltzik | 6-3 6-2 | | 0.69 | 6.3% | 6.3% | 59.4% | 55.3% | 30.8% | 11/16 | 1:15 |
| 3‑Jun‑2019 | Little Rock CH | Hard | R64 | 382 | 328 | Zhizhen Zhang [CHN] d. Hiltzik | 3-6 6-4 6-3 | | 0.90 | 4.3% | 8.6% | 55.9% | 71.2% | 46.3% | 5/8 | 1:51 |
| 29‑Apr‑2019 | Savannah CH | Clay | R64 | 379 | 408 | (WC)Sebastian Korda [USA] d. Hiltzik | 6-4 6-0 | | 0.60 | 0.0% | 2.4% | 64.3% | 51.9% | 40.0% | 0/4 | 1:00 |
| 15‑Apr‑2019 | Sarasota CH | Clay | R64 | 381 | 636 | (WC)Jenson Brooksby [USA] d. (WC)Hiltzik | 6-1 6-2 | | 0.59 | 12.8% | 8.5% | 57.4% | 70.4% | 20.0% | 9/13 | 1:04 |
| 11‑Mar‑2019 | Drummondville CH | Hard | R64 | 355 | 299 | Liam Broady [GBR] d. Hiltzik | 7-5 6-1 | | 0.64 | 4.1% | 2.0% | 49.0% | 75.0% | 40.0% | 0/3 | 1:07 |
| 4‑Feb‑2019 | Dallas CH | Hard | R16 | 352 | 130 | (6)Bjorn Fratangelo [USA] d. Hiltzik | 7-6(3) 7-6(2) | | 0.83 | 17.1% | 1.4% | 67.1% | 80.9% | 47.8% | 0/1 | 1:33 |
| 4‑Feb‑2019 | Dallas CH | Hard | R32 | 352 | 176 | Hiltzik d. (11)Roberto Quiroz [ECU] | 6-2 4-6 6-0 | | 1.37 | 13.9% | 1.4% | 69.4% | 74.0% | 45.5% | 3/5 | 1:30 |
| 4‑Feb‑2019 | Dallas CH | Hard | R64 | 352 | 270 | Hiltzik d. Kaichi Uchida [JPN] | 6-2 4-6 7-5 | | 1.19 | 20.4% | 1.0% | 63.3% | 72.6% | 44.4% | 6/10 | 1:48 |
| 28‑Jan‑2019 | Cleveland CH | Hard | QF | 357 | 247 | (15)Marcos Giron [USA] d. (Q)Hiltzik | 7-6(4) 6-4 | | 0.72 | 15.1% | 5.5% | 53.4% | 76.9% | 44.1% | 2/4 | 1:17 |
| 28‑Jan‑2019 | Cleveland CH | Hard | R16 | 357 | 178 | (Q)Hiltzik d. (7)Roberto Quiroz [ECU] | 6-4 6-2 | | 1.68 | 22.4% | 10.2% | 51.0% | 88.0% | 54.2% | 0/1 | 0:57 |
| 28‑Jan‑2019 | Cleveland CH | Hard | R32 | 357 | 223 | (Q)Hiltzik d. (11)Thomaz Bellucci [BRA] | 4-6 6-4 6-1 | | 1.16 | 10.1% | 2.2% | 51.7% | 78.3% | 51.2% | 4/5 | 1:59 |
| 28‑Jan‑2019 | Cleveland CH | Hard | R64 | 357 | 602 | (Q)Hiltzik d. (ITF)Matias Franco Descotte [ARG] | 4-6 7-5 7-5 | | 1.28 | 13.7% | 3.2% | 58.9% | 80.4% | 48.7% | 1/4 | 2:49 |
| 28‑Jan‑2019 | Cleveland CH | Hard | Q1 | 357 | | (1)Hiltzik d. (WC)Justin Boulais [CAN] | 6-3 7-6(7) | | 2.02 | 17.2% | 1.7% | 63.8% | 89.2% | 76.2% | 0/0 | 1:12 |
| 21‑Jan‑2019 | M25 Palm Coast FL | Clay | R16 | 357 | 578 | Or Ram Harel [ISR] d. (2)Hiltzik | 6-3 6-3 | | | | | | | | | |
| 21‑Jan‑2019 | M25 Palm Coast FL | Clay | R32 | 357 | 524 | (2)Hiltzik d. Sebastian Korda [USA] | 6-1 7-5 | | | | | | | | | |
| 31‑Dec‑2018 | Orlando CH | Hard | R64 | 356 | 400 | (P)Joao Souza [BRA] d. (WC)Hiltzik | 2-6 7-5 6-1 | | | | | | | | | |