| Challenger New Haven | 09/04 19:40 | 25 | [108] Bradley Klahn v Ulises Blanch [414] | 7-6,5-7,7-6 | |
| US Open | 08/28 15:00 | 24 | [108] Bradley Klahn v Kei Nishikori [7] | 2-6,6-4,3-6,5-7 | |
| US Open | 08/26 15:00 | 23 | [101] Thiago Monteiro v Bradley Klahn [108] | 3-6,2-6,3-6 | |
| ATP Cincinnati | 08/10 14:00 | 45 | [56] Casper Ruud v Bradley Klahn [92] | 7-6,7-5 | |
| ATP Montreal | 08/06 16:00 | 24 | [16] Marin Cilic v Bradley Klahn [92] | 6-3,7-6 | |
| ATP Montreal | 08/04 19:05 | 46 | [204] Steven Diez v Bradley Klahn [93] | 6-7,6-7 | |
| ATP Montreal | 08/03 19:30 | 45 | [151] Viktor Troicki v Bradley Klahn [93] | 5-7,3-6 | |
| ATP Washington | 07/29 22:55 | 24 | [72] Alexander Bublik v Bradley Klahn [93] | 7-6,6-3 | |
| ATP Atlanta | 07/25 19:35 | 26 | [34] Alex De Minaur v Bradley Klahn [94] | 6-4,6-4 | |
| ATP Atlanta | 07/22 20:45 | 25 | [94] Bradley Klahn v Marius Copil [84] | 7-6,7-5 | |
| ATP Newport | 07/16 15:00 | 25 | [100] Denis Kudla v Bradley Klahn [84] | 6-4,7-6 | |
| Challenger Winnetka | 07/14 19:00 | 29 | [87] Bradley Klahn v Jason Kubler [188] | 6-2,7-5 | |
| Challenger Winnetka | 07/13 19:00 | 28 | [87] Bradley Klahn v Denis Istomin [115] | 6-2,6-3 | |
| Challenger Winnetka | 07/12 15:00 | 27 | [87] Bradley Klahn v Bjorn Fratangelo [133] | 6-4,7-6 | |
| Challenger Winnetka | 07/11 20:35 | 26 | [87] Bradley Klahn v Donald Young [197] | 6-1,6-3 | |
| Challenger Winnetka | 07/10 17:10 | 25 | [87] Bradley Klahn v Max Purcell [264] | 7-5,6-3 | |
| Wimbledon | 07/01 16:45 | 23 | [87] Bradley Klahn v David Goffin [23] | 4-6,4-6,4-6 | |
| ATP Antalya | 06/25 10:30 | 26 | [45] Jordan Thompson v Bradley Klahn [89] | 7-6,6-3 | |
| ATP Antalya | 06/24 10:30 | 25 | [89] Bradley Klahn v Steve Darcis [230] | 6-3,6-2 | |
| ATP Queens | 06/15 10:00 | 64 | [138] Tommy Paul v Bradley Klahn [89] | 6-1,6-4 | |
| ATP Hertogenbosch | 06/08 16:35 | 64 | [89] Bradley Klahn v Andrea Arnaboldi [205] | 6-4,4-6,2-6 | |
| French Open | 05/27 09:00 | 23 | [25] Alex De Minaur v Bradley Klahn [89] | 6-1,6-4,6-4 | |
| ATP Geneva | 05/18 11:20 | 64 | [232] Bernabe Zapata Miralles v Bradley Klahn [87] | 5-7,6-4,6-2 | |
| ATP Rome | 05/11 17:00 | 45 | [43] Benoit Paire v Bradley Klahn [84] | 6-4,6-2 | |
| Challenger Sarasota | 04/17 18:40 | 25 | [92] Bradley Klahn v Daniel Elahi Galan [201] | 3-6,3-6 | |
| ATP Houston | 04/09 20:55 | 25 | [224] Santiago Giraldo v Bradley Klahn [93] | 6-4,6-4 | |
| Challenger Monterrey | 04/05 21:55 | 27 | [217] Donald Young v Bradley Klahn [96] | 7-5,6-4 | |
| Challenger Monterrey | 04/04 17:00 | 26 | [170] Sebastian Ofner v Bradley Klahn [96] | 3-6,3-6 | |
| Challenger Monterrey | 04/03 18:50 | 25 | [331] Evan Song v Bradley Klahn [96] | 4-6,3-6 | |
| ATP Miami | 03/20 18:50 | 23 | [453] Janko Tipsarevic v Bradley Klahn [93] | 6-3,6-3 |