| US Open, New York, USA | 08/27 16:50 | 23 | [11] Isner, John v Klahn, Bradley [92] | 7-6,6-3,6-4 | |
| Cincinnati, USA | 08/15 18:15 | 25 | [102] Klahn, Bradley v Carreno-Busta, Pablo [13] | 4-6,4-6 | |
| Cincinnati, USA | 08/13 18:55 | 24 | [45] Maximilian Marterer v Klahn, Bradley [102] | 6-7,4-6 | |
| ATP Cincinnati Qual | 08/12 14:00 | 46 | [116] Klahn, Bradley v Garcia-Lopez, Guillermo [73] | 7-6,7-6 | |
| ATP Cincinnati Qual | 08/11 14:30 | 45 | [61] Tennys Sandgren v Klahn, Bradley [116] | 4-6,6-7 | |
| Toronto, Canada | 08/08 23:35 | 25 | [116] Klahn, Bradley v Alexander Zverev [3] | 4-6,4-6 | |
| Toronto, Canada | 08/06 17:40 | 24 | [116] Klahn, Bradley v FERRER D. [69] | 7-6,6-4 | |
| ATP Toronto Qual | 08/05 16:00 | 46 | [115] Klahn, Bradley v Mirza Basic [83] | 6-1,7-6 | |
| ATP Toronto Qual | 08/04 19:50 | 45 | [115] Klahn, Bradley v Bernard Tomic [153] | Retired | |
| Binghamton, USA | 07/26 13:55 | 25 | Torpegaard, Mikael v Klahn, Bradley | 7-6,7-6 | |
| Gatineau, Canada | 07/22 17:30 | 29 | [257] Ugo Humbert v Klahn, Bradley [143] | 3-6,6-7 | |
| Gatineau, Canada | 07/21 16:30 | 28 | [143] Klahn, Bradley v Jason Kubler [114] | 6-2,6-3 | |
| Gatineau, Canada | 07/20 18:00 | 27 | [143] Klahn, Bradley v Li, Zhe [287] | 6-7,6-4,6-3 | |
| Gatineau, Canada | 07/18 17:20 | 26 | [143] Klahn, Bradley v Yunseong Chung [354] | 7-5,6-4 | |
| Gatineau, Canada | 07/16 16:40 | 25 | [143] Klahn, Bradley v Mousley, Bradley [318] | 7-5,7-6 | |
| Wimbledon, London, Great Britain | 07/05 16:20 | 24 | [17] Kyle Edmund v Klahn, Bradley [168] | 6-4,7-6,6-2 | |
| Wimbledon, London, Great Britain | 07/03 12:15 | 23 | [69] Sugita, Yuichi v Klahn, Bradley [168] | 6-2,6-7,2-6,2-6 | |
| Wimbledon Qual | 06/28 11:35 | 45 | [153] Bolelli, Simone v Klahn, Bradley [170] | 3-6,4-6,6-7 | |
| Wimbledon Qual | 06/26 16:20 | 45 | [170] Klahn, Bradley v Antoine Hoang [232] | 6-4,6-1 | |
| Wimbledon Qual | 06/25 14:05 | 44 | [163] Klahn, Bradley v Ojeda Lara, Ricardo [200] | 6-3,6-2 | |
| Ilkley, Great Britain | 06/19 14:00 | 25 | [167] Tatsuma Ito v Klahn, Bradley [163] | 6-4,6-7,6-3 | |
| s-Hertogenbosch, Netherlands, Qualifying | 06/09 10:05 | 64 | [216] Max Purcell v Klahn, Bradley [158] | 6-2,6-2 | |
| French Open Qual | 05/22 08:00 | 44 | [159] Klahn, Bradley v Laaksonen, Henri [140] | 6-4,6-7,4-6 | |
| Challenger - Bordeaux | 05/18 15:00 | 27 | [120] Guido Andreozzi v Klahn, Bradley [170] | 6-3,6-3 | |
| Challenger - Bordeaux | 05/17 12:10 | 26 | [170] Klahn, Bradley v Calvin Hemery [123] | 6-3,7-6 | |
| Challenger - Bordeaux | 05/15 08:00 | 25 | [296] Ugo Humbert v Klahn, Bradley [170] | 2-6,2-6 | |
| Challenger - Aix en Provence | 05/09 09:00 | 26 | [173] Klahn, Bradley v Thiago Monteiro [122] | 5-7,4-6 | |
| Challenger - Aix en Provence | 05/07 09:30 | 25 | [143] Alexander Bublik v Klahn, Bradley [173] | 6-7,6-7 | |
| ATP Houston Qual | 04/08 16:00 | - | [379] Yoshihito Nishioka v Klahn, Bradley [165] | 6-2,6-0 | |
| ATP Houston Qual | 04/07 17:30 | 26 | [287] Christopher Eubanks v Klahn, Bradley [165] | 6-7,6-4,6-7 |