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