Stadium: Center Court Round: 24 Ground: Hardcourt outdoor
| Challenger Columbus | 2019/06/10 21:25 | Jared Hiltzik v Evan Song | 3-6,2-6 |
| Challenger Little Rock | 2019/06/03 17:50 | Jared Hiltzik v Zhizhen Zhang | 6-3,4-6,3-6 |
| Challenger Savannah | 2019/04/29 21:40 | Jared Hiltzik v Sebastian Korda | 4-6,0-6 |
| Challenger Sarasota | 2019/04/15 21:00 | Jared Hiltzik v Jenson Brooksby | 1-6,2-6 |
| Challenger Drummondville | 2019/03/11 16:15 | Jared Hiltzik v Liam Broady | 5-7,1-6 |
| Challenger Dallas | 2019/02/07 16:00 | Bjorn Fratangelo v Jared Hiltzik | 7-6,7-6 |
| Challenger Dallas | 2019/02/06 18:55 | Jared Hiltzik v Roberto Quiroz | 6-2,4-6,6-0 |
| Challenger Dallas | 2019/02/04 21:50 | Jared Hiltzik v Kaichi Uchida | 6-2,4-6,7-5 |
| Wimbledon | 2019/06/26 11:25 | Corentin Moutet v Tim Smyczek | 6-1,6-3 |
| Wimbledon | 2019/06/24 10:00 | Mitchell Krueger v Tim Smyczek | 5-7,4-6 |
| Challenger Columbus | 2019/06/13 18:00 | Mikael Torpegaard v Tim Smyczek | 6-2,6-1 |
| Challenger Columbus | 2019/06/12 14:00 | Zsombor Piros v Tim Smyczek | 3-6,6-4,2-6 |
| Challenger Little Rock | 2019/06/07 19:05 | Tim Smyczek v Christopher Eubanks | 6-7,3-6 |
| Challenger Little Rock | 2019/06/04 15:00 | Tim Smyczek v Roy Smith | 3-6,7-5,6-1 |
| French Open | 2019/05/20 12:10 | Guillermo Garcia-Lopez v Tim Smyczek | 6-1,6-4 |
| Challenger Indian Wells | 2019/02/25 21:40 | Christian Harrison v Tim Smyczek | 6-4,4-6,6-3 |