| Montreal, Canada | 08/10 16:30 | 26 | [66] Donaldson, Jared v Diego Schwartzman [36] | 6-0,5-7,5-7 | |
| Montreal, Canada | 08/08 23:15 | 25 | [66] Donaldson, Jared v Benoit Paire [41] | 6-2,7-5 | |
| Montreal, Canada | 08/07 16:30 | 24 | [18] Lucas Pouille v Donaldson, Jared [66] | 6-7,6-7 | |
| Washington, USA | 08/03 20:00 | 26 | [69] Donaldson, Jared v Sock, Jack [19] | 6-7,2-6 | |
| Washington, USA | 08/02 20:05 | 25 | [209] Marc Polmans v Donaldson, Jared [69] | 2-6,3-6 | |
| Washington, USA | 07/31 22:15 | 24 | [74] Sela, Dudi v Donaldson, Jared [69] | 7-6,4-6,3-6 | |
| Atlanta, USA | 07/28 00:55 | 26 | [461] Christopher Eubanks v Donaldson, Jared [59] | 6-4,4-6,6-2 | |
| Atlanta, USA | 07/25 01:00 | 25 | [69] Ernesto Escobedo v Donaldson, Jared [59] | 3-6,1-6 | |
| Wimbledon, London, Great Britain | 07/08 17:00 | 25 | [8] Dominic Thiem v Donaldson, Jared [67] | 7-5,6-4,6-2 | |
| Wimbledon, London, Great Britain | 07/06 16:15 | 24 | [67] Donaldson, Jared v Lorenzi, Paolo [33] | 6-4,7-6,6-7,6-2 | |
| Wimbledon, London, Great Britain | 07/04 17:45 | 23 | [63] Tipsarevic, Janko v Donaldson, Jared [67] | Retired | |
| Eastbourne, Great Britain | 06/28 12:55 | 26 | [47] Young, Donald v Donaldson, Jared [65] | 6-4,7-5 | |
| Eastbourne, Great Britain | 06/26 10:00 | 25 | [65] Donaldson, Jared v Diego Schwartzman [37] | 7-6,3-6,7-5 | |
| ATP Queens Qual | 06/17 10:00 | 45 | [70] Donaldson, Jared v Kamke, Tobias [164] | 1-6,6-7 | |
| Open de France | 05/29 16:00 | 23 | Pierre-Hugues Herbert v Donaldson, Jared | 6-4,7-6,6-4 | |
| ATP - Genève | 05/23 17:50 | 26 | [62] Anderson, Kevin v Donaldson, Jared [72] | 6-3,6-7,6-2 | |
| ATP - Genève | 05/22 14:00 | 25 | Donaldson, Jared v Estrella Burgos, Victor | 6-2,6-4 | |
| ATP - Rome | 05/15 19:45 | 24 | [42] Harrison, Ryan v Donaldson, Jared [71] | 2-6,7-6,6-3 | |
| ATP Rome Qual | 05/14 10:50 | 46 | [50] Adrian Mannarino v Donaldson, Jared [78] | 6-4,6-1 | |
| ATP Rome Qual | 05/13 10:05 | 45 | [104] Marius Copil v Donaldson, Jared [78] | 6-1,3-6,4-6 | |
| ATP - Madrid | 05/09 16:05 | 25 | [78] Donaldson, Jared v Dominic Thiem [9] | 3-6,4-6 | |
| ATP - Madrid | 05/08 16:25 | 24 | [78] Donaldson, Jared v Adrian Mannarino [50] | 7-5,6-3 | |
| ATP Madrid Qual | 05/07 11:05 | 46 | [74] Istomin, Denis v Donaldson, Jared [79] | 7-6,6-4 | |
| ATP Madrid Qual | 05/06 13:10 | 45 | [90] Estrella Burgos, Victor v Donaldson, Jared [79] | 1-6,5-7 | |
| Challenger - Sarasota | 04/21 19:45 | 27 | [74] Donaldson, Jared v Millot, Vincent [170] | 4-6,5-7 | |
| Challenger - Sarasota | 04/19 23:00 | 26 | [74] Donaldson, Jared v Blaz Rola [264] | 6-4,3-6,6-4 | |
| Challenger - Sarasota | 04/18 00:20 | 25 | [74] Donaldson, Jared v Novikov, Dennis [189] | 6-2,6-4 | |
| ATP - Houston | 04/12 16:00 | 25 | [73] Donaldson, Jared v Gonzalez, Maximo [163] | 4-6,7-5,3-6 | |
| ATP - Miami | 03/28 16:25 | 26 | [17] Sock, Jack v Donaldson, Jared [95] | 6-2,6-1 | |
| ATP - Miami | 03/26 16:25 | 25 | [95] Donaldson, Jared v Milos Raonic [5] | Walkover |