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