| Wimbledon Qual | 06/25 14:35 | 44 | [208] Max Purcell v Young, Donald [135] | 3-6,2-6 | |
| Ilkley, Great Britain | 06/19 11:30 | 25 | [135] Young, Donald v Jason Kubler [162] | 4-6,6-7 | |
| s-Hertogenbosch, Netherlands, Qualifying | 06/09 10:15 | 64 | Young, Donald v Niesten, Miliaan | 4-6,2-6 | |
| French Open Qual | 05/21 08:00 | 44 | [377] Alexandre Muller v Young, Donald [137] | 7-6,6-3 | |
| Challenger - Savannah | 05/01 21:35 | 25 | [214] Garin, Cristian v Young, Donald [130] | 6-3,4-6,6-1 | |
| Challenger - Sarasota | 04/18 20:30 | 26 | [170] Stefan Kozlov v Young, Donald [131] | 6-4,6-4 | |
| Challenger - Sarasota | 04/16 15:45 | 25 | [361] Federico Coria v Young, Donald [131] | 4-6,6-7 | |
| ATP - Houston | 04/10 19:00 | 25 | [87] Nicolas Kicker v Young, Donald [130] | 6-3,6-2 | |
| ATP - Miami | 03/22 16:25 | 23 | [45] Mayer, Leonardo v Young, Donald [110] | 3-6,6-4,6-2 | |
| ATP - Indian Wells | 03/08 21:25 | 23 | Borna Coric v Young, Donald | 6-0,6-2 | |
| ATP - Acapulco | 02/27 23:40 | 25 | Chung, Hyeon v Young, Donald | 7-6,6-1 | |
| ATP - Delray Beach | 02/21 17:00 | 26 | Evgeny Donskoy v Young, Donald | 7-6,6-3 | |
| ATP - Delray Beach | 02/19 20:55 | 25 | Ramkumar Ramanathan v Young, Donald | 1-6,2-6 | |
| New York, USA | 02/13 00:30 | 25 | Harrison, Ryan v Young, Donald | 6-3,7-6 | |
| Open d'Australie | 01/16 04:00 | 23 | Novak Djokovic v Young, Donald | 6-1,6-2,6-4 | |
| ATP - Auckland | 01/07 23:30 | 25 | Young, Donald v Joao Sousa | 7-6,4-6,2-6 | |
| Basel, Switzerland | 10/25 15:35 | 25 | Young, Donald v Benneteau, Julien | 4-6,2-6 | |
| ATP Shanghai Qual | 10/08 05:45 | 46 | [59] Young, Donald v Dusan Lajovic [78] | 3-6,2-6 | |
| ATP Shanghai Qual | 10/07 05:40 | 45 | [59] Young, Donald v Polansky, Peter [122] | 6-1,6-4 | |
| ATP Tokyo | 10/03 05:00 | 25 | [29] Diego Schwartzman v Young, Donald [59] | 6-2,7-5 | |
| ATP Shenzhen | 09/29 09:55 | 27 | [61] Young, Donald v David Goffin [12] | 2-6,3-6 | |
| ATP Shenzhen | 09/27 12:55 | 26 | [61] Young, Donald v Chardy, Jérémy [86] | 7-6,6-4 | |
| ATP Shenzhen | 09/26 10:30 | 25 | [61] Young, Donald v Nicola Kuhn [230] | 7-5,7-6 | |
| US Open, New York, USA | 08/31 19:40 | 24 | [57] Young, Donald v Gaël Monfils [22] | 3-6,7-6,4-6,6-2,5-7 | |
| US Open, New York, USA | 08/29 15:00 | 23 | [125] Maximilian Marterer v Young, Donald [57] | 3-6,6-1,1-6,4-6 | |
| Winston-Salem, USA | 08/22 19:00 | 25 | [57] Young, Donald v Borna Coric [62] | 6-4,4-6,2-6 | |
| Winston-Salem, USA | 08/21 19:00 | 24 | Dutra Silva, Rogerio v Young, Donald | 4-6,2-6 | |
| Cincinnati, USA | 08/14 15:00 | 24 | [57] Young, Donald v Tommy Paul [175] | 4-6,6-7 | |
| Montreal, Canada | 08/07 18:05 | 24 | [61] Young, Donald v Benoit Paire [41] | 3-6,7-5,4-6 | |
| Washington, USA | 08/02 03:25 | 25 | [58] Young, Donald v Kei Nishikori [9] | 3-6,6-4,6-7 |