| ATP - Miami | 03/18 17:50 | 44 | [197] Donaldson, Jared v Andrey Rublev [99] | 2-6,3-6 | |
| ATP - Indian Wells | 03/11 01:00 | 24 | [192] Donaldson, Jared v Rafael Nadal [2] | 1-6,1-6 | |
| ATP - Indian Wells | 03/09 00:10 | 23 | [148] Tatsuma Ito v Donaldson, Jared [192] | 3-6,5-7 | |
| Challenger - Indian Wells | 02/27 20:20 | 25 | [243] Giraldo, Santiago v Donaldson, Jared [129] | 6-2,2-6,6-4 | |
| ATP - Delray Beach | 02/19 16:00 | 25 | [101] Garcia-Lopez, Guillermo v Donaldson, Jared [120] | 2-6,6-3,6-3 | |
| US Open, New York, USA | 08/27 15:00 | 23 | Milos Raonic v Donaldson, Jared | Cancelled | |
| Toronto, Canada | 08/06 15:00 | 24 | [62] Donaldson, Jared v Benoit Paire [55] | 3-6,4-6 | |
| Washington, USA | 08/01 20:30 | 25 | [32] Stefanos Tsitsipas v Donaldson, Jared [62] | 3-6,6-3,7-5 | |
| Washington, USA | 07/31 20:20 | 24 | [62] Donaldson, Jared v Jordan Thompson [97] | 6-4,7-6 | |
| Wimbledon, London, Great Britain | 07/04 15:10 | 24 | [35] Stefanos Tsitsipas v Donaldson, Jared [54] | 6-3,6-2,3-6,4-6,6-3 | |
| Wimbledon, London, Great Britain | 07/02 15:15 | 23 | [61] Jaziri, Malek v Donaldson, Jared [54] | 6-7,3-6,1-6 | |
| Eastbourne, Great Britain | 06/27 10:00 | 26 | [54] Donaldson, Jared v Denis Shapovalov [26] | 4-6,6-4,2-6 | |
| Eastbourne, Great Britain | 06/25 10:00 | 25 | [55] Donaldson, Jared v Taylor Fritz [69] | 6-7,6-3,7-6 | |
| London, Great Britain | 06/18 13:20 | 25 | [55] Donaldson, Jared v Frances Tiafoe [62] | 4-6,6-7 | |
| French Open, Paris, France | 05/30 12:15 | 24 | [57] Donaldson, Jared v Grigor Dimitrov [5] | 7-6,4-6,6-4,4-6,8-10 | |
| French Open, Paris, France | 05/27 10:35 | 23 | [59] Nicolas Jarry v Donaldson, Jared [57] | 3-6,6-4,6-3,3-6,4-6 | |
| Geneva, Switzerland | 05/23 19:10 | 26 | [25] Stan Wawrinka v Donaldson, Jared [57] | 6-3,6-4 | |
| Geneva, Switzerland | 05/21 10:00 | 25 | [57] Donaldson, Jared v Istomin, Denis [98] | 5-7,6-4,6-0 | |
| ATP - Rome | 05/14 09:00 | 24 | [55] Donaldson, Jared v Carreno-Busta, Pablo [11] | 4-6,6-3,0-6 | |
| ATP - Madrid | 05/08 10:00 | 24 | Bautista-Agut, Roberto v Donaldson, Jared | 6-7,6-4,6-4 | |
| ATP - Barcelone | 04/23 12:00 | 24 | [51] Donaldson, Jared v Dutra Silva, Rogerio [125] | 3-6,1-6 | |
| ATP - Monte-Carlo | 04/16 09:00 | 24 | Donaldson, Jared v Ramos-Vinolas, Albert | 3-6,3-6 | |
| ATP - Miami | 03/25 15:00 | 25 | [80] Joao Sousa v Donaldson, Jared [49] | 1-6,6-3,6-4 | |
| ATP - Miami | 03/23 19:55 | 24 | [49] Donaldson, Jared v Lopez, Feliciano [32] | 6-4,6-2 | |
| ATP - Miami | 03/21 23:30 | 23 | [49] Donaldson, Jared v Baghdatis, Marcos [82] | 6-3,6-4 | |
| Irving, USA | 03/16 01:25 | 26 | Mikhail Kukushkin v Donaldson, Jared | 6-3,6-3 | |
| Irving, USA | 03/14 18:25 | 25 | Radu Albot v Donaldson, Jared | 4-6,6-7 | |
| ATP - Indian Wells | 03/11 00:10 | 24 | Donaldson, Jared v Bautista-Agut, Roberto | 4-6,2-6 | |
| ATP - Indian Wells | 03/09 02:35 | 23 | Donaldson, Jared v King, Evan | 6-1,4-6,6-4 | |
| ATP - Acapulco | 03/03 00:05 | 28 | Donaldson, Jared v Anderson, Kevin | 3-6,6-4,3-6 |