| Challenger Fairfield | 10/12 17:00 | 26 | [91] Ernesto Escobedo v Bradley Klahn [313] | 4-6,7-6,3-6 | |
| Challenger Fairfield | 10/10 21:15 | 25 | [313] Bradley Klahn v Kevin King [215] | 1-6,6-1,6-1 | |
| Challenger Monterrey | 10/08 21:15 | 29 | [429] Bradley Klahn v Maximilian Marterer [132] | 6-7,6-7 | |
| Challenger Monterrey | 10/07 19:45 | 28 | [429] Bradley Klahn v Quentin Halys [124] | 7-5,7-6 | |
| Challenger Monterrey | 10/06 20:50 | 27 | [81] Victor E Burgos v Bradley Klahn [429] | 2-6,6-4,4-6 | |
| Challenger Monterrey | 10/06 01:25 | 26 | [268] Austin Krajicek v Bradley Klahn [429] | 6-4,6-7,3-6 | |
| Challenger Monterrey | 10/03 18:00 | 25 | [429] Bradley Klahn v Dennis Novikov [217] | Retired | |
| Challenger Gwangju | 09/20 01:30 | 26 | [447] Bradley Klahn v Tatsuma Ito [162] | 5-7,6-1,3-6 | |
| Challenger Gwangju | 09/19 03:45 | 25 | [298] Ti Chen v Bradley Klahn [447] | 2-6,2-6 | |
| Challenger Shanghai | 09/12 02:00 | 25 | [447] Bradley Klahn v Tatsuma Ito [165] | 6-3,2-6,6-7 | |
| US Open Qual | 08/24 15:00 | 45 | [475] Bradley Klahn v Guido Andreozzi [150] | 4-6,7-6,4-6 | |
| US Open Qual | 08/22 18:05 | 44 | [475] Bradley Klahn v Marc Polmans [236] | 6-2,0-6,6-2 | |
| Challenger Gatineau | 07/18 16:00 | 25 | [471] Bradley Klahn v Brayden Schnur [213] | 3-6,6-7 | |
| Challenger Winnetka | 07/11 15:00 | 25 | [184] Ramkumar Ramanathan v Bradley Klahn [497] | 3-6,7-6,7-6 | |
| Wimbledon Qual | 06/28 16:40 | 45 | [119] Darian King v Bradley Klahn [490] | 3-6,6-1,6-4 | |
| Wimbledon Qual | 06/26 10:00 | 44 | [490] Bradley Klahn v Soon Woo Kwon [192] | 6-3,6-4 | |
| Challenger Vicenza Qual | 05/27 12:50 | 45 | [213] Marcelo Arevalo v Bradley Klahn [477] | 7-5,6-4 | |
| French Open Qual | 05/24 15:20 | 45 | [477] Bradley Klahn v Bjorn Fratangelo [138] | 4-6,6-7 | |
| French Open Qual | 05/22 12:35 | 44 | [477] Bradley Klahn v John-Patrick Smith [223] | 6-2,6-3 | |
| Challenger Heilbronn Qual | 05/14 09:00 | 46 | [473] Bradley Klahn v Sebastian Fanselow [337] | 5-7,6-7 | |
| Challenger Heilbronn Qual | 05/13 08:00 | 45 | [393] Bernabe Zapata Miralles v Bradley Klahn [473] | 6-7,1-6 | |
| Challenger Tallahassee | 04/27 23:20 | 27 | [267] Andrea Arnaboldi v Bradley Klahn [478] | 6-2,7-6 | |
| Challenger Tallahassee | 04/26 15:00 | 26 | [395] Dominik Koepfer v Bradley Klahn [478] | 5-7,1-6 | |
| Challenger Tallahassee | 04/24 18:35 | 25 | [478] Bradley Klahn v Maximo Gonzalez [152] | 7-6,6-7,6-4 | |
| Challenger Sarasota Qual | 04/16 16:40 | 46 | [474] Bradley Klahn v Daniel Elahi Galan [393] | 6-7,5-7 | |
| Challenger Sarasota Qual | 04/15 15:20 | 45 | Bradley Klahn v Mark Oljaca | 6-3,6-3 | |
| ATP Houston Qual | 04/09 16:00 | 46 | [475] Bradley Klahn v Noah Rubin [182] | 2-6,6-3,6-7 | |
| ATP Houston Qual | 04/08 15:00 | 45 | [96] Renzo Olivo v Bradley Klahn [475] | Retired | |
| Challenger Panama City | 04/04 18:40 | 25 | [475] Bradley Klahn v Andrea Arnaboldi [307] | 2-6,5-7 | |
| ITF USA F11 | 03/26 20:00 | 29 | Sebastian Fanselow v Bradley Klahn | 6-3,6-2 |