| ATP - Metz | 09/17 12:00 | 25 | [39] Jan-Lennard Struff v Pierre-Hugues Herbert [55] | 6-7,4-6 | |
| Open dos EUA | 08/29 18:30 | 24 | [14] John Isner v Jan-Lennard Struff [37] | 6-3,7-6,7-6 | |
| Open dos EUA | 08/27 18:35 | 23 | [37] Jan-Lennard Struff v Casper Ruud [54] | 6-4,6-4,6-2 | |
| ATP - Cincinnati | 08/15 17:25 | 26 | [8] Daniil Medvedev v Jan-Lennard Struff [36] | 6-2,6-1 | |
| ATP - Cincinnati | 08/14 17:00 | 25 | [36] Jan-Lennard Struff v Stefanos Tsitsipas [7] | 6-4,6-7,7-6 | |
| ATP - Cincinnati | 08/12 19:35 | 24 | [80] Ivo Karlovic v Jan-Lennard Struff [36] | 5-7,6-7 | |
| ATP - Montreal | 08/06 23:00 | 25 | [17] Nikoloz Basilashvili v Jan-Lennard Struff [35] | 2-6,6-2,6-3 | |
| ATP - Montreal | 08/05 16:00 | 24 | [35] Jan-Lennard Struff v Jo-Wilfried Tsonga [60] | 6-2,6-2 | |
| ATP - Washington | 08/01 00:25 | 25 | [46] Jordan Thompson v Jan-Lennard Struff [35] | 6-7,6-4,7-5 | |
| ATP - Hamburgo | 07/25 12:25 | 26 | [59] Pablo Carreño-Busta v Jan-Lennard Struff [36] | 6-1,7-6 | |
| ATP - Hamburgo | 07/23 09:30 | 25 | [91] Thiago Monteiro v Jan-Lennard Struff [36] | 1-6,3-6 | |
| Wimbledon | 07/06 12:30 | 25 | [33] Jan-Lennard Struff v Mikhail Kukushkin [58] | 3-6,6-7,6-4,5-7 | |
| Wimbledon | 07/04 10:00 | 24 | [33] Jan-Lennard Struff v Taylor Fritz [31] | 6-4,6-3,5-7,7-6 | |
| Wimbledon | 07/02 14:40 | 23 | [33] Jan-Lennard Struff v Radu Albot [40] | 6-4,6-3,6-2 | |
| Wimbledon | 07/02 10:00 | 23 | Jan-Lennard Struff v Marcos Baghdatis | Cancelled | |
| ATP - Halle | 06/19 12:10 | 26 | [35] Jan-Lennard Struff v Karen Khachanov [9] | 3-6,6-3,4-6 | |
| ATP - Halle | 06/18 10:00 | 25 | [35] Jan-Lennard Struff v Laslo Djere [27] | 6-4,6-4 | |
| ATP - Estugarda | 06/15 11:00 | 28 | [38] Jan-Lennard Struff v Matteo Berrettini [30] | 4-6,5-7 | |
| ATP - Estugarda | 06/14 10:30 | 27 | [38] Jan-Lennard Struff v Lucas Pouille [26] | 6-4,6-4 | |
| ATP - Estugarda | 06/12 15:20 | 26 | [38] Jan-Lennard Struff v Miomir Kecmanovic [83] | 6-2,6-2 | |
| ATP - Estugarda | 06/11 09:00 | 25 | [25] Denis Shapovalov v Jan-Lennard Struff [38] | 5-7,4-6 | |
| Open de França | 06/03 10:50 | 26 | [1] Novak Djokovic v Jan-Lennard Struff [45] | 6-3,6-2,6-2 | |
| Open de França | 06/01 10:45 | 25 | [45] Jan-Lennard Struff v Borna Coric [15] | 4-6,6-1,4-6,7-6,11-9 | |
| Open de França | 05/30 12:50 | 24 | [45] Jan-Lennard Struff v Radu Albot [40] | 7-6,7-6,6-7,6-2 | |
| Open de França | 05/27 15:40 | 23 | [24] Denis Shapovalov v Jan-Lennard Struff [45] | 6-7,3-6,4-6 | |
| ATP - Roma | 05/16 16:35 | 26 | [51] Jan-Lennard Struff v Kei Nishikori [6] | 6-3,6-7,3-6 | |
| ATP - Roma | 05/16 10:15 | 25 | [10] Marin Čilić v Jan-Lennard Struff [51] | 2-6,3-6 | |
| ATP - Roma | 05/14 13:10 | 24 | [48] Grigor Dimitrov v Jan-Lennard Struff [51] | 4-6,7-6,3-6 | |
| ATP - Madrid | 05/07 13:50 | 25 | [11] Marin Čilić v Jan-Lennard Struff [49] | 4-6,6-3,6-4 | |
| ATP - Madrid | 05/05 10:50 | 24 | [34] Nick Kyrgios v Jan-Lennard Struff [48] | 6-7,4-6 |