| ATP - Šanghaj | 10/11 10:30 | 25 | [15] Kevin Anderson v Jan-Lennard Struff [58] | 6-7,6-7 | |
| ATP - Šanghaj | 10/10 06:30 | 24 | [15] Kevin Anderson v Adrian Mannarino [29] | 6-3,6-1 | |
| ATP - Tokio | 10/04 05:55 | 26 | [52] Ryan Harrison v Kevin Anderson [16] | 6-3,1-6,7-6 | |
| ATP - Tokio | 10/02 06:40 | 25 | [44] Gilles Simon v Kevin Anderson [15] | 2-6,6-7 | |
| US Open | 09/10 20:20 | 29 | [1] Rafael Nadal v Kevin Anderson [32] | 6-3,6-3,6-4 | |
| US Open | 09/08 20:00 | 28 | Kevin Anderson v Pablo Carreno-Busta | 4-6,7-5,6-3,6-4 | |
| US Open | 09/06 02:10 | 27 | [21] Sam Querrey v Kevin Anderson [32] | 6-7,7-6,3-6,6-7 | |
| US Open | 09/03 21:10 | 26 | [40] Paolo Lorenzi v Kevin Anderson [32] | 4-6,3-6,7-6,4-6 | |
| US Open | 09/01 18:45 | 25 | [32] Kevin Anderson v Borna Coric [61] | 6-4,6-3,6-2 | |
| US Open | 08/30 22:50 | 24 | [32] Kevin Anderson v Ernests Gulbis [255] | 6-3,7-5,6-4 | |
| US Open | 08/28 16:15 | 23 | Kevin Anderson v JC Aragone | 6-3,6-3,6-1 | |
| ATP - Cincinnati | 08/15 15:00 | 24 | Kevin Anderson v Alexandr Dolgopolov | 4-6,6-7 | |
| ATP - Montreal | 08/12 01:20 | 27 | [8] Alexander Zverev v Kevin Anderson [32] | 7-5,6-4 | |
| ATP - Montreal | 08/10 21:40 | 26 | [32] Kevin Anderson v Sam Querrey [20] | 6-4,6-1 | |
| ATP - Montreal | 08/09 19:35 | 25 | [15] Pablo C. Busta v Kevin Anderson [32] | 3-6,6-7 | |
| ATP - Montreal | 08/08 21:10 | 24 | [32] Kevin Anderson v Dudi Sela [77] | 6-3,7-6 | |
| ATP - Washington | 08/06 19:00 | 29 | [45] Kevin Anderson v Alexander Zverev [8] | 4-6,4-6 | |
| ATP - Washington | 08/05 18:05 | 28 | [45] Kevin Anderson v Jack Sock [19] | 6-3,6-4 | |
| ATP - Washington | 08/04 20:00 | 27 | [45] Kevin Anderson v Yuki Bhambri [200] | 6-4,4-6,6-3 | |
| ATP - Washington | 08/03 21:50 | 26 | [7] Dominic Thiem v Kevin Anderson [45] | 3-6,7-6,6-7 | |
| ATP - Washington | 08/02 23:05 | 25 | [73] Malek Jaziri v Kevin Anderson [45] | 4-6,1-6 | |
| Wimbledon | 07/10 12:45 | 26 | [28] Sam Querrey v Kevin Anderson [42] | 5-7,7-6,6-3,6-7,6-3 | |
| Wimbledon | 07/07 17:15 | 25 | [42] Kevin Anderson v Ruben Bemelmans [124] | 7-6,6-4,7-6 | |
| Wimbledon | 07/05 15:20 | 24 | [42] Kevin Anderson v Andreas Seppi [87] | 6-3,7-6,6-3 | |
| Wimbledon | 07/03 11:55 | 23 | [35] Fernando Verdasco v Kevin Anderson [42] | 6-2,6-7,6-7,3-6 | |
| ATP - Eastbourne | 06/29 09:30 | 26 | [27] Richard Gasquet v Kevin Anderson [45] | 6-4,6-4 | |
| ATP - Eastbourne | 06/26 12:20 | 25 | [53] Thomaz Bellucci v Kevin Anderson [45] | 3-6,1-6 | |
| French Open | 06/05 14:20 | 26 | [56] Kevin Anderson v Marin Čilić [8] | Retired | |
| French Open | 06/03 09:00 | 25 | [49] Kyle Edmund v Kevin Anderson [56] | 7-6,6-7,7-5,1-6,4-6 | |
| French Open | 06/01 13:15 | 24 | [56] Kevin Anderson v Nick Kyrgios [19] | 5-7,6-4,6-1,6-2 |