| US Open, New York, USA, Qualifying | 08/22 19:20 | 44 | [228] Klein, Brydan v Millot, Vincent [164] | 6-3,3-6,6-7 | |
| Challenger Vancouver Qual | 08/12 17:00 | - | Klein, Brydan v Thai-Son Kwiatkowski | 4-6,3-6 | |
| ATP Montreal Qual | 08/06 17:20 | 46 | [235] Klein, Brydan v Millot, Vincent [165] | 6-7,6-7 | |
| ATP Montreal Qual | 08/05 18:55 | 45 | Leduc, Antoine v Klein, Brydan | 0-6,3-6 | |
| ATP - Los Cabos | 08/02 01:40 | 25 | [235] Klein, Brydan v Millot, Vincent [165] | 2-6,6-3,1-6 | |
| ATP Los Cabos Qual | 07/31 00:50 | 46 | [154] Ebden, Matthew v Klein, Brydan [239] | 6-0,7-5 | |
| ATP Los Cabos Qual | 07/29 23:00 | 45 | [450] Hugo Nys v Klein, Brydan [239] | 6-3,2-6,3-6 | |
| ATP Atlanta Qual | 07/23 15:00 | 46 | [129] Stefan Kozlov v Klein, Brydan [226] | 6-7,6-2,7-6 | |
| ATP Atlanta Qual | 07/22 15:00 | 45 | Bryde, Trent v Klein, Brydan | 3-6,0-6 | |
| ATP Newport Qual | 07/16 16:20 | 45 | [263] Ebden, Matthew v Klein, Brydan [232] | 3-6,6-0,6-4 | |
| Wimbledon, London, Great Britain | 07/04 13:50 | 23 | [44] Sugita, Yuichi v Klein, Brydan [232] | 7-6,6-3,6-0 | |
| Ilkley, Great Britain | 06/19 14:00 | 25 | [228] Klein, Brydan v Norbert Gombos [91] | 6-1,6-7,4-6 | |
| Challenger - Nottingham | 06/15 16:35 | 26 | [209] Klein, Brydan v Groth, Sam [240] | 3-6,4-6 | |
| Challenger - Nottingham | 06/13 17:50 | 25 | [243] Alex De Minaur v Klein, Brydan [209] | 6-7,3-6 | |
| Challenger Surbiton Qual | 06/04 10:00 | 45 | [216] Klein, Brydan v Quiroz, Roberto [236] | 4-6,5-7 | |
| French Open Qual | 05/22 08:00 | 44 | [211] Klein, Brydan v Maximilian Marterer [130] | 2-6,2-6 | |
| Challenger - Busan | 05/17 05:10 | 26 | [291] Krajicek, Austin v Klein, Brydan [213] | 6-4,6-2 | |
| Challenger - Busan | 05/15 07:15 | 25 | [213] Klein, Brydan v Tepavac, Marko [369] | 6-3,6-0 | |
| Challenger Seoul | 05/09 01:30 | 25 | [219] Klein, Brydan v Bemelmans, Ruben [137] | 4-6,6-3,1-6 | |
| Challenger Gimcheon | 05/03 03:45 | 26 | [220] Klein, Brydan v Kavcic, Blaz [123] | 4-6,2-6 | |
| Challenger Gimcheon | 05/01 04:25 | 25 | Klein, Brydan v Yunseong Chung | 6-3,6-4 | |
| Challenger - Taipei | 04/19 03:00 | 25 | [393] Bachinger, Matthias v Klein, Brydan [222] | 6-4,6-2 | |
| ITF Indonesia F6 | 04/15 03:00 | 28 | [231] Klein, Brydan v Max Purcell [309] | Retired | |
| ITF Indonesia F6 | 04/14 03:00 | 27 | Klein, Brydan v Hung, Jui-Chen | 6-3,6-2 | |
| ITF Indonesia F6 | 04/13 08:00 | 26 | Klein, Brydan v Chiu, Yu Hsiang | 6-4,6-2 | |
| ITF Indonesia F6 | 04/12 04:20 | 25 | Klein, Brydan v Congsup Congcar | 6-0,6-3 | |
| ITF Indonesia F5 | 04/09 03:30 | 29 | [257] Chen, Ti v Klein, Brydan [247] | 3-6,7-6,6-3 | |
| ITF Indonesia F5 | 04/08 03:00 | 28 | Gray, Jonathan v Klein, Brydan | 4-6,6-4,1-6 | |
| ITF Indonesia F5 | 04/07 03:00 | 27 | Blake Ellis v Klein, Brydan | 3-6,3-6 | |
| ITF Indonesia F5 | 04/06 03:00 | 26 | Bava, Haadin v Klein, Brydan | 1-6,4-6 |