| ATP - Acapulco | 02/23 23:20 | 64 | Harrison, Ryan v Hernandez Serrano, Juan Alejandro | 7-5,6-2 | |
| ATP - Acapulco | 02/23 23:15 | 64 | Harrison, Ryan v Hernandez, Alejandro | Cancelled | |
| New York, USA | 02/13 17:55 | 26 | [111] Lorenzi, Paolo v Harrison, Ryan [92] | 4-6,6-4,6-4 | |
| New York, USA | 02/12 19:55 | 25 | [118] Polansky, Peter v Harrison, Ryan [92] | 3-6,4-6 | |
| Challenger Dallas | 02/07 02:45 | 25 | [271] Vilella Martinez, Mario v Harrison, Ryan [93] | Walkover | |
| Open d'Australie | 01/17 07:30 | 24 | [83] Harrison, Ryan v Daniil Medvedev [19] | 3-6,3-6,3-6 | |
| Open d'Australie | 01/15 00:00 | 23 | [90] Jiri Vesely v Harrison, Ryan [83] | 0-6,5-7,3-6 | |
| Sydney, Australia | 01/07 11:45 | 25 | [81] Harrison, Ryan v Yoshihito Nishioka [75] | 4-6,2-6 | |
| ATP Brisbane | 01/01 05:00 | 25 | [35] Kyrgios, Nick v Harrison, Ryan [62] | 7-6,5-7,7-6 | |
| Basel, Switzerland | 10/22 18:40 | 25 | [93] Marius Copil v Harrison, Ryan [59] | 6-2,7-6 | |
| Pékin, Chine | 10/02 06:30 | 25 | Harrison, Ryan v Grigor Dimitrov | Cancelled | |
| US Open, New York, USA | 08/27 21:15 | 23 | [53] Harrison, Ryan v Anderson, Kevin [5] | 6-7,7-5,6-4,3-6,4-6 | |
| Winston-Salem, USA | 08/23 23:00 | 27 | [57] Daniil Medvedev v Harrison, Ryan [56] | 7-6,6-4 | |
| Winston-Salem, USA | 08/23 01:10 | 26 | [56] Harrison, Ryan v Filip Krajinovic [32] | 6-3,7-6 | |
| Winston-Salem, USA | 08/22 18:00 | 25 | Simon, Gilles v Harrison, Ryan | Walkover | |
| Winston-Salem, USA | 08/20 23:00 | 24 | [56] Harrison, Ryan v Gojo, Borna [497] | 6-2,6-4 | |
| ATP Cincinnati Qual | 08/12 00:30 | 45 | [57] Harrison, Ryan v Hubert Hurkacz [112] | 3-6,3-6 | |
| Toronto, Canada | 08/08 16:00 | 25 | [57] Harrison, Ryan v Ilya Ivashka [125] | 6-7,4-6 | |
| Toronto, Canada | 08/07 16:15 | 24 | [83] Mackenzie McDonald v Harrison, Ryan [57] | 4-6,2-6 | |
| Toronto, Canada | 08/07 14:00 | - | Bautista-Agut, Roberto v Harrison, Ryan | Cancelled | |
| ATP Toronto Qual | 08/05 15:00 | 46 | [57] Harrison, Ryan v Mahut, Nicolas [128] | 6-1,6-2 | |
| ATP Toronto Qual | 08/04 15:00 | 45 | [57] Harrison, Ryan v Gulbis, Ernests [129] | 6-3,7-6 | |
| ATP - Los Cabos | 07/31 16:00 | 25 | Polansky, Peter v Harrison, Ryan | Cancelled | |
| Atlanta, USA | 07/29 21:00 | 29 | [9] Isner, John v Harrison, Ryan [53] | 5-7,6-3,6-4 | |
| Atlanta, USA | 07/28 23:00 | 28 | [53] Harrison, Ryan v Cameron Norrie [73] | 2-6,6-3,6-2 | |
| Atlanta, USA | 07/27 20:00 | 27 | [53] Harrison, Ryan v Chung, Hyeon [23] | 6-7,6-2,7-6 | |
| Atlanta, USA | 07/25 17:00 | 26 | [53] Harrison, Ryan v Lacko, Lukas [71] | 2-6,6-2,6-3 | |
| Atlanta, USA | 07/24 16:30 | 25 | Harrison, Ryan v James Duckworth | 4-6,7-6,6-1 | |
| Newport, USA | 07/17 18:05 | 25 | [55] Harrison, Ryan v Mahut, Nicolas [134] | Retired | |
| Wimbledon, London, Great Britain | 07/04 12:25 | 24 | [26] Adrian Mannarino v Harrison, Ryan [59] | 7-5,7-5,7-6 |