| ATP - Indian Wells | 03/09 19:00 | 24 | Maximilian Marterer v Anderson, Kevin | Cancelled | |
| Open d'Australie | 01/16 02:05 | 24 | [6] Anderson, Kevin v Frances Tiafoe [39] | 6-4,4-6,4-6,5-7 | |
| Open d'Australie | 01/14 00:00 | 23 | [6] Anderson, Kevin v Adrian Mannarino [41] | 6-3,5-7,6-2,6-1 | |
| Kooyong Classic | 01/09 00:00 | 1 | [7] Marin Cilic v Anderson, Kevin [6] | 6-3,4-6,15-13 | |
| ATP Pune | 01/05 11:30 | 29 | [6] Anderson, Kevin v Karlovic, Ivo [100] | 7-6,6-7,7-6 | |
| ATP Pune | 01/04 15:40 | 28 | [6] Anderson, Kevin v Simon, Gilles [30] | 6-3,7-6 | |
| ATP Pune | 01/03 13:35 | 27 | [6] Anderson, Kevin v Jaume Munar [81] | 6-3,6-3 | |
| ATP Pune | 01/02 11:30 | 26 | [6] Anderson, Kevin v Laslo Djere [93] | 7-6,7-6 | |
| Mubadala World Tennis Championship | 12/29 15:00 | 29 | [6] Anderson, Kevin v Novak Djokovic [1] | 6-4,5-7,5-7 | |
| Mubadala World Tennis Championship | 12/28 13:00 | 28 | [2] Rafael Nadal v Anderson, Kevin [6] | 6-4,3-6,4-6 | |
| Mubadala World Tennis Championship | 12/27 12:00 | 27 | [25] Chung, Hyeon v Anderson, Kevin [6] | 7-6,2-6,1-6 | |
| Tour Finals Turin, Italy | 11/17 20:00 | 28 | [1] Novak Djokovic v Anderson, Kevin [6] | 6-2,6-2 | |
| Tour Finals Turin, Italy | 11/15 20:00 | 3 | [3] Federer, Roger v Anderson, Kevin [6] | 6-4,6-3 | |
| Tour Finals Turin, Italy | 11/13 14:00 | 2 | [6] Anderson, Kevin v Kei Nishikori [9] | 6-0,6-1 | |
| Tour Finals Turin, Italy | 11/11 14:00 | 1 | [6] Anderson, Kevin v Dominic Thiem [8] | 6-3,7-6 | |
| Paris, France | 11/01 20:05 | 26 | [6] Anderson, Kevin v Kei Nishikori [11] | 4-6,4-6 | |
| Paris, France | 10/31 14:25 | 25 | [6] Anderson, Kevin v Nikoloz Basilashvili [22] | 6-3,6-7,7-6 | |
| ATP Vienna | 10/28 13:00 | 29 | [11] Kei Nishikori v Anderson, Kevin [8] | 3-6,6-7 | |
| ATP Vienna | 10/27 13:50 | 28 | [30] Verdasco, Fernando v Anderson, Kevin [8] | 3-6,6-3,4-6 | |
| ATP Vienna | 10/26 16:05 | 27 | [13] Borna Coric v Anderson, Kevin [8] | Retired | |
| ATP Vienna | 10/24 17:30 | 26 | Melzer, Jurgen v Anderson, Kevin | Walkover | |
| ATP Vienna | 10/22 16:15 | 25 | [24] Nikoloz Basilashvili v Anderson, Kevin [8] | 6-4,6-7,3-6 | |
| Shanghai, Chine | 10/12 06:30 | 27 | [8] Anderson, Kevin v Novak Djokovic [3] | 6-7,3-6 | |
| Shanghai, Chine | 10/11 06:50 | 26 | [8] Anderson, Kevin v Stefanos Tsitsipas [15] | 6-4,7-6 | |
| Shanghai, Chine | 10/10 08:45 | 25 | [8] Anderson, Kevin v Mikhail Kukushkin [83] | 6-3,6-2 | |
| ATP Tokyo | 10/05 10:40 | 27 | [25] Richard Gasquet v Anderson, Kevin [9] | 7-6,7-6 | |
| ATP Tokyo | 10/04 08:20 | 26 | [41] Frances Tiafoe v Anderson, Kevin [9] | 3-6,6-3,2-6 | |
| ATP Tokyo | 10/03 04:30 | 25 | [48] Ebden, Matthew v Anderson, Kevin [9] | 6-4,6-7,2-6 | |
| Laver Cup, Matchs en Simple | 09/23 21:25 | 44 | [5] Alexander Zverev v Anderson, Kevin [9] | 6-7,7-5,10-7 | |
| Laver Cup, Matchs en Simple | 09/23 00:00 | 44 | [3] Novak Djokovic v Anderson, Kevin [9] | 6-7,7-5,6-10 |