| ATP - Viena | 10/31 13:00 | 28 | [111] Kevin Anderson v Andrey Rublev [8] | Retired | |
| ATP - Viena | 10/30 13:00 | 27 | [111] Kevin Anderson v Daniil Medvedev [6] | 6-4,7-6 | |
| ATP - Viena | 10/28 19:10 | 26 | [15] Pablo Carreño Busta v Kevin Anderson [111] | 5-7,1-6 | |
| ATP - Viena | 10/26 13:00 | 25 | [92] Dennis Novak v Kevin Anderson [111] | 7-6,4-6,6-7 | |
| Open de França | 10/03 09:00 | 25 | [118] Kevin Anderson v Andrey Rublev [12] | 3-6,2-6,3-6 | |
| Open de França | 10/01 14:50 | 24 | [24] Dusan Lajovic v Kevin Anderson [118] | 2-6,4-6,6-4,6-3,3-6 | |
| Open de França | 09/29 11:00 | 23 | [73] Laslo Djere v Kevin Anderson [118] | 2-6,3-6,4-6 | |
| ATP - Hamburgo | 09/21 12:10 | 25 | [59] Tommy Paul v Kevin Anderson [119] | 6-4,0-6,6-4 | |
| ATP - Roma | 09/14 13:20 | 24 | [119] Kevin Anderson v Ugo Humbert [42] | 3-6,6-7 | |
| Open dos EUA | 08/31 17:25 | 23 | [117] Kevin Anderson v Alexander Zverev [7] | 6-7,7-5,3-6,5-7 | |
| ATP - Nova Iorque | 08/23 21:15 | 25 | [123] Kevin Anderson v Stefanos Tsitsipas [6] | 1-6,3-6 | |
| ATP - Nova Iorque | 08/22 16:35 | 24 | [44] Kyle Edmund v Kevin Anderson [123] | 6-7,6-4,3-6 | |
| ATP - Nova Iorque | 02/12 02:10 | 25 | [131] Jason Jung v Kevin Anderson [120] | 7-6,6-4 | |
| Open da Austrália | 01/23 08:15 | 24 | [34] Taylor Fritz v Kevin Anderson [122] | 4-6,6-7,7-6,6-2,6-2 | |
| Open da Austrália | 01/21 10:25 | 23 | [149] Ilya Ivashka v Kevin Anderson [122] | 4-6,6-2,6-4,4-6,6-7 | |
| Taça ATP | 01/08 10:10 | 2 | [24] Benoit Paire v Kevin Anderson [147] | 6-2,6-7,6-7 | |
| Taça ATP | 01/08 09:00 | 2 | Gael Monfils v Kevin Anderson | Cancelled | |
| Taça ATP | 01/06 01:45 | 2 | [147] Kevin Anderson v Cristian Garin [33] | 6-0,6-3 | |
| Taça ATP | 01/04 10:10 | 2 | [2] Novak Djokovic v Kevin Anderson [91] | 7-6,7-6 | |
| Open dos EUA | 08/26 18:15 | 23 | Zachary Svajda v Kevin Anderson | Cancelled | |
| ATP - Washington | 07/31 17:00 | 25 | [11] Kevin Anderson v Adrian Mannarino [66] | Cancelled | |
| Wimbledon | 07/05 12:00 | 25 | [8] Kevin Anderson v Guido Pella [26] | 4-6,3-6,6-7 | |
| Wimbledon | 07/03 15:45 | 24 | [8] Kevin Anderson v Janko Tipsarevic [288] | 6-4,6-7,6-1,6-4 | |
| Wimbledon | 07/01 10:00 | 23 | [8] Kevin Anderson v Pierre-Hugues Herbert [39] | 6-3,6-4,6-2 | |
| ATP - Queens | 06/20 10:00 | 26 | [38] Gilles Simon v Kevin Anderson [8] | 6-1,4-6,6-4 | |
| ATP - Queens | 06/17 14:15 | 25 | [49] Cameron Norrie v Kevin Anderson [8] | 6-4,6-7,4-6 | |
| ATP - Miami | 03/28 23:40 | 27 | [7] Kevin Anderson v Roger Federer [5] | 0-6,4-6 | |
| ATP - Miami | 03/26 20:15 | 26 | [7] Kevin Anderson v Jordan Thompson [77] | 7-5,7-5 | |
| ATP - Miami | 03/25 16:00 | 25 | [7] Kevin Anderson v Joao Sousa [41] | 6-4,7-6 | |
| ATP - Miami | 03/23 17:20 | 24 | [7] Kevin Anderson v Jaume Munar [61] | 6-4,3-6,6-3 |