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