| WTA San Diego | 10/08 22:55 | 14 | [27] Shuai Zhang v Robin Montgomery [297] | 2-6,3-6 | |
| ITF W80 Rancho Santa Fe | 10/06 18:30 | 26 | [297] Robin Montgomery v Elvina Kalieva [219] | 2-6,6-2,6-7 | |
| ITF W80 Rancho Santa Fe | 10/05 19:40 | 25 | [214] Catherine Harrison v Robin Montgomery [297] | 4-6,6-7 | |
| ITF W60 Templeton | 10/02 20:45 | 29 | [51] Madison Brengle v Robin Montgomery [359] | 4-6,6-4,6-2 | |
| ITF W60 Templeton | 10/01 19:45 | 28 | [359] Robin Montgomery v Kateryna Bondarenko [438] | 6-3,6-1 | |
| ITF W60 Templeton | 09/30 21:55 | 27 | [163] Katarzyna Kawa v Robin Montgomery [359] | 3-6,1-6 | |
| ITF W60 Templeton | 09/29 21:30 | 26 | [359] Robin Montgomery v Victoria Duval [382] | 6-1,6-2 | |
| ITF W60 Templeton | 09/28 23:00 | 25 | [359] Robin Montgomery v Himeno Sakatsume [338] | 6-2,3-6,6-2 | |
| ITF W60 Templeton | 09/27 19:20 | 54 | [359] Robin Montgomery v Alexandra Osborne [296] | 7-5,6-1 | |
| ITF W60 Templeton | 09/26 21:40 | 54 | Robin Montgomery v Kendra Bunch | 6-2,6-1 | |
| ITF W60 Berkeley | 09/22 21:15 | 26 | [194] Louisa Chirico v Robin Montgomery [383] | 3-6,6-2,6-4 | |
| ITF W60 Berkeley | 09/21 17:55 | 25 | Rachel Gailis v Robin Montgomery | 4-6,3-6 | |
| ITF W60 Berkeley | 09/20 16:45 | 54 | [383] Robin Montgomery v Alexandra Osborne [296] | 6-2,6-1 | |
| ITF W60 Berkeley | 09/19 17:00 | 54 | Robin Montgomery v Rhiann Newborn | 6-3,6-3 | |
| ITF W60 Poertschach | 06/07 09:35 | 25 | [192] Viktoria Kuzmova v Robin Montgomery [377] | 7-6,6-1 | |
| ITF W60 Poertschach | 06/06 08:00 | 54 | [377] Robin Montgomery v Sina Herrmann [452] | 6-4,6-0 | |
| ITF W60 Poertschach | 06/05 09:25 | 54 | Robin Montgomery v Sarah Rebecca Sekulic | 6-2,6-3 | |
| ITF W25 Annenheim | 06/03 08:00 | 27 | [341] Lena Papadakis v Robin Montgomery [376] | 6-2,6-2 | |
| ITF W25 Annenheim | 06/02 09:45 | 26 | [447] Jessie Aney v Robin Montgomery [376] | 2-6,6-2,3-6 | |
| ITF W25 Annenheim | 06/01 13:15 | 25 | [376] Robin Montgomery v En Shuo Liang [289] | 6-4,6-1 | |
| ITF W25 Nottingham | 05/13 10:30 | 27 | [361] Eden Silva v Robin Montgomery [378] | 6-3,6-4 | |
| ITF W25 Nottingham | 05/12 12:35 | 26 | [378] Robin Montgomery v Pemra Ozgen [325] | 6-4,6-2 | |
| ITF W25 Nottingham | 05/10 10:00 | 25 | Ho Ching Wu v Robin Montgomery | 4-6,4-6 | |
| ITF W25 Nottingham | 05/03 09:00 | 25 | [431] Robin Montgomery v Fanni Stollar [360] | 5-7,5-7 | |
| ITF W25 Nottingham | 04/24 09:00 | 29 | [451] Eden Silva v Robin Montgomery [433] | 6-4,6-4 | |
| ITF W25 Nottingham | 04/23 11:10 | 28 | [433] Robin Montgomery v Katherine Sebov [330] | Retired | |
| ITF W25 Nottingham | 04/22 13:10 | 27 | [433] Robin Montgomery v Joanna Garland [441] | 6-3,6-3 | |
| ITF W25 Nottingham | 04/21 09:00 | 26 | [314] Urszula Radwanska v Robin Montgomery [433] | 6-7,2-6 | |
| ITF W25 Nottingham | 04/19 09:00 | 25 | Andre Lukosiute v Robin Montgomery | 6-1,6-7,5-7 | |
| WTA Miami | 03/23 16:55 | 23 | [439] Robin Montgomery v Anna Kalinskaya [84] | 6-4,4-6,6-7 |