| US Open | 08/25 20:55 | 15 | Kevin Anderson v Tomas Machac | 4-6,5-7 | |
| US Open | 08/22 21:05 | 14 | Kevin Anderson v Oleksii Krutykh | 6-3,7-5 | |
| ATP - Washington | 08/01 21:45 | 24 | Kevin Anderson v Jordan Thompson | 4-6,7-6,1-6 | |
| ATP - Newport | 07/20 19:55 | 27 | Kevin Anderson v Ugo Humbert | 2-6,4-6 | |
| ATP - Newport | 07/19 16:30 | 26 | Gijs Brouwer v Kevin Anderson | 3-6,6-7 | |
| ATP - Newport | 07/18 20:10 | 25 | Gabriel Diallo v Kevin Anderson | 3-6,2-6 | |
| ATP - Miami | 03/25 15:00 | 24 | [122] Juan Manuel Cerundolo v Kevin Anderson [91] | 7-6,3-6,6-3 | |
| ATP - Miami | 03/22 15:00 | 19 | [90] Kevin Anderson v Mitchell Krueger [164] | 6-7,5-7 | |
| ATP - Miami | 03/21 16:30 | 14 | [90] Kevin Anderson v Alex Bolt [188] | 6-3,6-4 | |
| ATP - Indian Wells | 03/09 01:35 | 14 | [90] Kevin Anderson v Christopher O'Connell [149] | 6-3,2-6,2-6 | |
| ATP - Acapulco | 02/21 00:00 | 19 | [93] Kevin Anderson v Jeffrey John Wolf [216] | 7-6,4-6,3-6 | |
| ATP - Acapulco | 02/20 00:00 | 14 | Kevin Anderson v Nicolas Mejia | 6-3,7-6 | |
| ATP - Delray Beach | 02/15 01:00 | 25 | [99] Steve Johnson v Kevin Anderson [93] | 6-2,6-7,6-2 | |
| ATP - Dallas | 02/10 01:00 | 26 | [101] Kevin Anderson v John Isner [26] | 6-7,7-6,6-7 | |
| ATP - Dallas | 02/07 22:00 | 25 | [101] Kevin Anderson v Sam Querrey [118] | 6-4,6-4 | |
| Australian Open | 01/17 07:45 | 23 | [29] Reilly Opelka v Kevin Anderson [97] | 6-3,6-4,7-6 | |
| ATP - Melbourne | 01/05 08:00 | 25 | [77] Jaume Munar v Kevin Anderson [80] | 6-4,6-4 | |
| ATP - Paríž | 10/30 10:05 | 14 | [61] Kevin Anderson v Hugo Gaston [107] | 6-7,6-2,6-7 | |
| ATP - Viedeň | 10/25 14:55 | 25 | [32] Alex De Minaur v Kevin Anderson [61] | 6-3,7-6 | |
| ATP - Viedeň | 10/24 13:20 | 19 | [60] Kevin Anderson v Roberto Carballes Baena [80] | 7-5,4-6,7-6 | |
| ATP - Viedeň | 10/23 15:15 | 14 | [60] Kevin Anderson v Jurij Rodionov [132] | 6-1,6-4 | |
| ATP - Indian Wells | 10/13 01:00 | 25 | [18] Gael Monfils v Kevin Anderson [69] | 7-5,6-2 | |
| ATP - Indian Wells | 10/10 18:00 | 24 | [69] Kevin Anderson v Lorenzo Sonego [21] | 7-6,7-6 | |
| ATP - Indian Wells | 10/08 20:00 | 23 | [69] Kevin Anderson v Jordan Thompson [76] | 7-5,6-2 | |
| ATP - San Diego | 09/29 18:30 | 25 | [69] Kevin Anderson v Daniel Evans [22] | 6-7,5-7 | |
| ATP - San Diego | 09/26 21:55 | - | [68] Kevin Anderson v Alex Bolt [147] | 7-6,3-6,5-7 | |
| ATP - San Diego | 09/25 23:45 | 26 | [68] Kevin Anderson v Jason Kubler [219] | 6-3,7-5 | |
| US Open | 09/01 23:00 | 24 | [77] Kevin Anderson v Diego Schwartzman [14] | 6-7,3-6,4-6 | |
| US Open | 08/30 15:00 | 23 | [90] Jiří Veselý v Kevin Anderson [77] | 6-7,6-4,6-3,6-7,6-7 | |
| ATP - Cincinnati | 08/17 01:25 | 24 | [76] Kevin Anderson v Karen Khachanov [30] | 2-6,4-6 |