| US Open | 09/02 15:00 | 26 | [9] Dominic Thiem v Kevin Anderson [5] | 7-5,6-2,7-6 | |
| US Open | 08/31 18:55 | 25 | [28] Denis Shapovalov v Kevin Anderson [5] | 6-4,3-6,4-6,6-4,4-6 | |
| US Open | 08/29 20:45 | 24 | [46] Jeremy Chardy v Kevin Anderson [5] | 2-6,4-6,4-6 | |
| 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 Cincinnati | 08/17 15:00 | 26 | [6] Kevin Anderson v David Goffin [11] | 2-6,4-6 | |
| ATP Cincinnati | 08/15 17:35 | 25 | [6] Kevin Anderson v Jeremy Chardy [46] | 7-6,6-2 | |
| ATP Toronto | 08/11 19:00 | 28 | [6] Kevin Anderson v Stefanos Tsitsipas [27] | 7-6,4-6,6-7 | |
| ATP Toronto | 08/10 16:30 | 27 | [5] Grigor Dimitrov v Kevin Anderson [6] | 2-6,2-6 | |
| ATP Toronto | 08/09 16:45 | 26 | [125] Ilya Ivashka v Kevin Anderson [6] | 5-7,3-6 | |
| ATP Toronto | 08/08 21:00 | 25 | [87] Evgeny Donskoy v Kevin Anderson [6] | 6-4,2-6,6-7 | |
| Wimbledon | 07/15 13:00 | 29 | [8] Kevin Anderson v Novak Djokovic [21] | 2-6,2-6,6-7 | |
| Wimbledon | 07/13 12:00 | 28 | [8] Kevin Anderson v John Isner [10] | 7-6,6-7,6-7,6-4,26-24 | |
| Wimbledon | 07/11 12:00 | 27 | [2] Roger Federer v Kevin Anderson [8] | 6-2,7-6,5-7,4-6,11-13 | |
| Wimbledon | 07/09 14:05 | 26 | [44] Gael Monfils v Kevin Anderson [8] | 6-7,6-7,7-5,6-7 | |
| Wimbledon | 07/06 10:30 | 25 | [27] Philipp Kohlschreiber v Kevin Anderson [8] | 3-6,5-7,5-7 | |
| Wimbledon | 07/04 15:25 | 24 | [50] Andreas Seppi v Kevin Anderson [8] | 3-6,7-6,3-6,4-6 | |
| Wimbledon | 07/02 15:10 | 23 | [190] Norbert Gombos v Kevin Anderson [8] | 3-6,4-6,4-6 | |
| Boodles Challenge | 06/26 14:30 | 1 | [8] Kevin Anderson v Fabio Fognini [16] | 6-1,6-2 | |
| ATP Queen's | 06/19 11:30 | 25 | [38] Leonardo Mayer v Kevin Anderson [8] | 7-6,4-6,7-6 | |
| French Open | 06/04 09:00 | 26 | [12] Diego Schwartzman v Kevin Anderson [7] | 1-6,2-6,7-5,7-6,6-2 | |
| French Open | 06/02 11:25 | 25 | [64] Mischa Zverev v Kevin Anderson [7] | 1-6,7-6,3-6,6-7 | |
| French Open | 05/31 11:50 | 24 | [75] Pablo Cuevas v Kevin Anderson [7] | 3-6,6-3,6-7,4-6 | |
| French Open | 05/29 09:00 | 23 | [74] Paolo Lorenzi v Kevin Anderson [7] | 1-6,2-6,4-6 | |
| ATP Roma | 05/16 14:35 | 25 | [7] Kevin Anderson v Aljaz Bedene [65] | Retired | |
| ATP Madrid | 05/12 14:00 | 28 | [7] Dominic Thiem v Kevin Anderson [8] | 6-4,6-2 | |
| ATP Madrid | 05/11 11:00 | 27 | [95] Dusan Lajovic v Kevin Anderson [8] | 6-7,6-3,3-6 | |
| ATP Madrid | 05/10 12:20 | 26 | [28] Philipp Kohlschreiber v Kevin Anderson [8] | 3-6,6-7 | |
| ATP Madrid | 05/09 10:00 | 25 | [96] Mikhail Kukushkin v Kevin Anderson [8] | 7-5,6-7,2-6 | |
| ATP Estoril | 05/03 15:30 | 26 | [8] Kevin Anderson v Stefanos Tsitsipas [44] | 7-6,3-6,3-6 | |
| ATP Miami | 03/29 19:00 | 27 | [19] Pablo Carreno-Busta v Kevin Anderson [8] | 6-4,5-7,7-6 |