| ATP Cincinnati | 08/15 15:00 | 19 | [75] Kevin Anderson v Steve Johnson [78] | 7-6,6-4 | |
| ATP Cincinnati | 08/14 14:00 | 14 | [62] Lorenzo Musetti v Kevin Anderson [75] | 3-6,3-6 | |
| ATP Washington | 08/02 19:45 | 24 | [75] Kevin Anderson v Jenson Brooksby [130] | 6-7,3-6 | |
| ATP Atlanta | 07/28 02:15 | 25 | [75] Kevin Anderson v Nick Kyrgios [58] | 6-7,3-6 | |
| ATP Newport | 07/18 18:30 | 29 | [113] Kevin Anderson v Jenson Brooksby [152] | 7-6,6-4 | |
| ATP Newport | 07/17 17:00 | 28 | [37] Alexander Bublik v Kevin Anderson [113] | 6-4,6-7,5-7 | |
| ATP Newport | 07/15 18:20 | 27 | [231] Jack Sock v Kevin Anderson [113] | 7-6,2-6,4-6 | |
| ATP Newport | 07/14 15:00 | 26 | [167] Sebastian Ofner v Kevin Anderson [113] | 5-7,6-7 | |
| ATP Newport | 07/12 20:15 | 25 | [156] Illya Marchenko v Kevin Anderson [113] | 5-7,3-6 | |
| Wimbledon | 06/30 12:30 | 24 | [1] Novak Djokovic v Kevin Anderson [102] | 6-3,6-3,6-3 | |
| Wimbledon | 06/28 14:30 | 23 | [209] Marcelo Tomas Barrios Vera v Kevin Anderson [102] | 7-6,4-6,4-6,6-7 | |
| ATP Eastbourne | 06/19 10:00 | 14 | [280] Max Purcell v Kevin Anderson [101] | 7-6,4-6,6-3 | |
| Challenger Nottingham | 06/15 12:50 | 25 | [118] Denis Kudla v Kevin Anderson [101] | 7-5,1-6,6-3 | |
| Challenger Nottingham | 06/11 13:25 | 27 | [228] Marius Copil v Kevin Anderson [100] | 7-6,7-6 | |
| Challenger Nottingham | 06/10 17:15 | 26 | [186] Lukas Rosol v Kevin Anderson [100] | 3-6,4-6 | |
| Challenger Nottingham | 06/08 14:00 | 25 | [229] Jay Clarke v Kevin Anderson [100] | 3-6,6-7 | |
| French Open | 06/01 15:25 | 23 | [100] Kevin Anderson v Soonwoo Kwon [91] | 5-7,4-6,6-2,6-7 | |
| ATP Estoril | 04/30 12:15 | 27 | [42] Marin Cilic v Kevin Anderson [105] | Retired | |
| ATP Estoril | 04/28 09:30 | 26 | [105] Kevin Anderson v Roberto Carballes Baena [93] | 6-3,7-6 | |
| ATP Estoril | 04/28 09:30 | 26 | Kevin Anderson v Kei Nishikori | Cancelled | |
| ATP Estoril | 04/26 15:15 | 25 | [105] Kevin Anderson v Frances Tiafoe [64] | 4-6,7-6,7-6 | |
| ATP Miami | 03/25 21:10 | 23 | [91] Kevin Anderson v Damir Dzumhur [126] | 6-7,5-7 | |
| ATP Miami | 03/25 19:25 | 23 | Kevin Anderson v Thiago Monteiro | Cancelled | |
| ATP Acapulco | 03/16 16:00 | 25 | Kevin Anderson v Frances Tiafoe | Cancelled | |
| Australian Open | 02/09 08:00 | 23 | [81] Kevin Anderson v Matteo Berrettini [10] | 6-7,5-7,3-6 | |
| ATP Great Ocean Road Open | 02/04 23:30 | 26 | [82] Kevin Anderson v Karen Khachanov [20] | 3-6,6-7 | |
| ATP Great Ocean Road Open | 02/03 10:30 | 25 | [82] Kevin Anderson v Cedrik-Marcel Stebe [128] | 6-4,6-2 | |
| ATP Great Ocean Road Open | 02/01 07:00 | 24 | [63] Feliciano Lopez v Kevin Anderson [82] | 4-6,5-7 | |
| ATP Paris | 11/04 10:00 | 25 | [86] Kevin Anderson v Daniil Medvedev [5] | Retired | |
| ATP Paris | 11/03 11:25 | 24 | [54] Laslo Djere v Kevin Anderson [86] | Retired |