| Challenger de New Haven | 09/02 15:25 | 24 | [197] Donald Young v Filip Peliwo [299] | 6-3,6-4 | |
| US Open | 08/20 16:15 | 44 | [198] Donald Young v Jason Jung [121] | 3-6,7-6,5-7 | |
| Challenger de Aptos | 08/05 20:20 | 24 | [202] Donald Young v Lukas Lacko [227] | 4-6,2-6 | |
| ATP Washington | 07/30 01:50 | 24 | [44] Hubert Hurkacz v Donald Young [195] | 6-1,6-4 | |
| ATP Washington | 07/28 14:00 | 64 | [122] Peter Gojowczyk v Donald Young [190] | 6-2,3-6,4-6 | |
| ATP Washington | 07/27 16:10 | 45 | Nicholas Reyes v Donald Young | 2-6,0-6 | |
| ATP Atlanta | 07/21 18:50 | 164 | [187] Donald Young v Jason Jung [127] | 1-6,6-7 | |
| ATP Atlanta | 07/20 17:15 | 64 | [117] Dominik Koepfer v Donald Young [187] | 6-3,4-6,3-6 | |
| Challenger de Winnetka | 07/11 20:35 | 26 | [87] Bradley Klahn v Donald Young [197] | 6-1,6-3 | |
| Challenger de Winnetka | 07/11 01:10 | 25 | [381] Sekou Bangoura v Donald Young [197] | 3-6,4-6 | |
| Wimbledon | 06/27 10:00 | 25 | [171] Ruben Bemelmans v Donald Young [200] | 6-4,6-4,6-1 | |
| Wimbledon | 06/26 10:00 | 45 | [200] Donald Young v Daniel Elahi Galan [198] | 7-6,6-3 | |
| Wimbledon | 06/24 14:20 | 44 | [200] Donald Young v Egor Gerasimov [170] | 6-4,7-6 | |
| Challenger de Columbus | 06/12 20:00 | 25 | [198] Donald Young v Dennis Novikov [400] | 6-7,2-6 | |
| Challenger de Little Rock | 06/05 16:35 | 25 | [193] Donald Young v Zhizhen Zhang [328] | 4-6,6-3,3-6 | |
| Open de Francia | 05/20 08:00 | 44 | [162] Marcos Giron v Donald Young [197] | 6-0,6-1 | |
| Challenger de Puerto Vallarta | 05/01 18:00 | 25 | [348] Alexander Sarkissian v Donald Young [195] | 1-6,7-6,6-2 | |
| Challenger de León | 04/24 16:00 | 25 | [337] Gonzalo Escobar v Donald Young [199] | 6-3,7-5 | |
| Challenger de Monterrey | 04/06 21:35 | 28 | [309] Emilio Gomez v Donald Young [217] | 2-6,6-3,6-4 | |
| Challenger de Monterrey | 04/05 21:55 | 27 | [217] Donald Young v Bradley Klahn [96] | 7-5,6-4 | |
| Challenger de Monterrey | 04/04 23:05 | 26 | [217] Donald Young v Santiago Giraldo [230] | 6-3,6-4 | |
| Challenger de Monterrey | 04/04 00:45 | 25 | [106] Paolo Lorenzi v Donald Young [217] | 4-6,3-6 | |
| Challenger de Monterrey | 04/02 00:50 | 24 | [217] Donald Young v Roberto O-Olmedo [280] | 6-4,6-4 | |
| ATP Indian Wells | 03/08 19:00 | 23 | [206] Donald Young v Hubert Hurkacz [67] | 3-6,3-6 | |
| Challenger de Indian Wells | 02/28 18:00 | 26 | [214] Donald Young v Lloyd Harris [99] | 4-6,2-6 | |
| Challenger de Indian Wells | 02/26 21:45 | 25 | [122] Henri Laaksonen v Donald Young [214] | 5-7,6-3,4-6 | |
| Challenger de Indian Wells | 02/25 19:30 | 24 | [265] Thai-Son Kwiatkowski v Donald Young [214] | 6-4,1-6,6-7 | |
| ATP Delray Beach | 02/17 17:45 | 164 | [201] Donald Young v Daniel Evans [147] | 2-6,6-7 | |
| ATP Delray Beach | 02/16 18:35 | 64 | [117] Bjorn Fratangelo v Donald Young [201] | 2-6,6-7 | |
| Challenger de Cleveland | 01/30 02:55 | 25 | [332] Roy Smith v Donald Young [203] | 6-4,0-6,7-6 |