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