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