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