| ATP Paris | 10/30 10:00 | 24 | [45] Ryan Harrison v Peter Gojowczyk [62] | 6-7,3-6 | |
| ATP Basel | 10/25 13:40 | 26 | Roberto Bautista-Agut v Ryan Harrison | 6-3,7-6 | |
| ATP Basel | 10/24 17:20 | 25 | Alexandr Dolgopolov v Ryan Harrison | 4-6,1-6 | |
| ATP Shanghai | 10/11 05:00 | 25 | [46] Ryan Harrison v Grigor Dimitrov [9] | 6-3,3-6,6-7 | |
| ATP Shanghai | 10/10 05:00 | 24 | [221] Ze Zhang v Ryan Harrison [46] | 2-6,3-6 | |
| ATP Tokyo | 10/06 06:50 | 27 | [5] Marin Cilic v Ryan Harrison [52] | 6-2,6-0 | |
| ATP Tokyo | 10/04 05:55 | 26 | [52] Ryan Harrison v Kevin Anderson [16] | 6-3,1-6,7-6 | |
| ATP Tokyo | 10/02 06:05 | 25 | [259] Yusuke Takahashi v Ryan Harrison [51] | 4-6,6-4,4-6 | |
| US Open | 08/30 15:00 | 23 | [45] Ryan Harrison v Tomas Berdych [18] | 4-6,2-6,6-7 | |
| ATP Cincinnati | 08/13 18:40 | 24 | [44] Ryan Harrison v Gilles Muller [21] | 4-6,7-5,6-7 | |
| ATP Montreal | 08/09 16:30 | 25 | [44] Ryan Harrison v Roberto Bautista-Agut [16] | 5-7,2-6 | |
| ATP Montreal | 08/07 19:25 | 24 | [91] Thomas Fabbiano v Ryan Harrison [44] | 3-6,5-7 | |
| ATP Washington | 08/02 22:50 | 25 | [77] Marcos Baghdatis v Ryan Harrison [40] | 6-4,6-1 | |
| ATP Atlanta | 07/30 21:00 | 29 | [42] Ryan Harrison v John Isner [20] | 6-7,6-7 | |
| ATP Atlanta | 07/29 23:00 | 28 | [45] Kyle Edmund v Ryan Harrison [42] | 7-6,3-6,4-6 | |
| ATP Atlanta | 07/28 19:55 | 27 | [42] Ryan Harrison v Christopher Eubanks [461] | 6-1,6-2 | |
| ATP Atlanta | 07/27 20:25 | 26 | [42] Ryan Harrison v John Millman [174] | 6-7,7-6,7-5 | |
| Wimbledon | 07/06 14:50 | 24 | [41] Ryan Harrison v Tomas Berdych [15] | 4-6,3-6,7-6,3-6 | |
| Wimbledon | 07/04 15:30 | 23 | [45] Borna Coric v Ryan Harrison [41] | 6-7,4-6,6-7 | |
| ATP Eastbourne | 06/27 10:00 | 25 | [30] Mischa Zverev v Ryan Harrison [41] | 6-4,7-6 | |
| ATP Queens | 06/19 12:30 | 25 | [11] Grigor Dimitrov v Ryan Harrison [41] | 6-3,6-1 | |
| French Open | 05/29 09:00 | 23 | [52] Aljaz Bedene v Ryan Harrison [42] | 6-4,6-0,3-6,6-1 | |
| ATP Geneva | 05/23 12:35 | 25 | [61] Janko Tipsarevic v Ryan Harrison [42] | 6-4,7-6 | |
| ATP Rome | 05/16 18:40 | 25 | [42] Ryan Harrison v Marin Cilic [8] | 3-6,2-6 | |
| ATP Rome | 05/15 19:45 | 24 | [42] Ryan Harrison v Jared Donaldson [71] | 2-6,7-6,6-3 | |
| ATP Madrid | 05/10 10:00 | 25 | [20] Nick Kyrgios v Ryan Harrison [47] | 6-3,6-3 | |
| ATP Madrid | 05/09 10:00 | 24 | [47] Ryan Harrison v Bernard Tomic [39] | 7-5,4-6,6-2 | |
| ATP Estoril | 05/05 14:50 | 27 | [31] David Ferrer v Ryan Harrison [52] | 6-4,6-0 | |
| ATP Estoril | 05/05 09:00 | 26 | Ryan Harrison v Juan Martin Del Potro | Walkover | |
| ATP Estoril | 05/02 15:10 | 25 | [52] Ryan Harrison v Guillermo Garcia-Lopez [120] | 6-3,2-6,6-2 |