Stadium: Court 2 Round: 24 Ground: Grass
| Wimbledon, London, Great Britain | 2019/07/01 10:00 | Anderson, Kevin v Pierre-Hugues Herbert | 6-3,6-4,6-2 |
| London, Great Britain | 2019/06/20 10:00 | Simon, Gilles v Anderson, Kevin | 6-1,4-6,6-4 |
| London, Great Britain | 2019/06/17 14:15 | Cameron Norrie v Anderson, Kevin | 6-4,6-7,4-6 |
| ATP - Miami | 2019/03/28 23:40 | Anderson, Kevin v Federer, Roger | 0-6,4-6 |
| ATP - Miami | 2019/03/26 20:15 | Anderson, Kevin v Jordan Thompson | 7-5,7-5 |
| ATP - Miami | 2019/03/25 16:00 | Anderson, Kevin v Joao Sousa | 6-4,7-6 |
| ATP - Miami | 2019/03/23 17:20 | Anderson, Kevin v Jaume Munar | 6-4,3-6,6-3 |
| Open d'Australie | 2019/01/16 02:05 | Anderson, Kevin v Frances Tiafoe | 6-4,4-6,4-6,5-7 |
| Wimbledon, London, Great Britain | 2019/07/01 10:00 | Tipsarevic, Janko v Yoshihito Nishioka | 6-4,6-7,6-2,5-7,6-2 |
| Antalya, Turquie | 2019/06/24 10:30 | Gunneswaran, Prajnesh v Tipsarevic, Janko | 6-0,7-6 |
| Open de France | 2019/05/26 10:15 | Tipsarevic, Janko v Grigor Dimitrov | 3-6,0-6,6-3,7-6,4-6 |
| ATP - Genève | 2019/05/21 18:40 | Tipsarevic, Janko v Hugo Dellien | 6-7,3-6 |
| ATP - Genève | 2019/05/20 16:55 | Gojowczyk, Peter v Tipsarevic, Janko | 5-7,5-7 |
| Challenger - San Luis Potosí | 2019/04/17 21:10 | Lucas Miedler v Tipsarevic, Janko | 7-5,3-6,6-3 |
| Challenger - San Luis Potosí | 2019/04/17 00:55 | Tipsarevic, Janko v Gomez, Lucas | 6-4,5-7,6-2 |
| ATP - Houston | 2019/04/12 18:30 | Querrey, Sam v Tipsarevic, Janko | 7-6,7-6 |