| WTA Miami | 03/23 16:55 | 23 | [439] Robin Montgomery v Anna Kalinskaya [84] | 6-4,4-6,6-7 | |
| WTA Indian Wells | 03/09 19:00 | 23 | [361] Robin Montgomery v Kaia Kanepi [63] | 3-6,3-6 | |
| ITF - Arcadia W60 | 03/03 17:55 | 26 | [142] Rebecca Marino v Robin Montgomery [369] | 6-4,6-3 | |
| ITF - Arcadia W60 | 03/02 20:00 | 25 | [194] Jamie Loeb v Robin Montgomery [369] | 6-7,6-7 | |
| ITF - Arcadia W60 | 03/01 17:55 | 54 | Robin Montgomery v Vivian Wolff | 6-2,7-6 | |
| ITF - Arcadia W60 | 02/28 18:15 | 54 | Robin Montgomery v Ariana Anazagasty-Pursoo | 6-1,6-4 | |
| ITF - Rome, GA W60 | 02/01 18:50 | 25 | [388] Robin Montgomery v Emina Bektas [204] | 6-7,3-6 | |
| ITF - Orlando W60 | 01/27 17:05 | 25 | [369] Robin Montgomery v Xiyu Wang [139] | 6-3,3-6,2-6 | |
| ITF - Orlando W60 | 01/25 15:00 | 54 | [256] Allie Kiick v Robin Montgomery [369] | 2-6,5-7 | |
| ITF - Orlando W60 | 01/24 15:00 | 54 | Lauren Proctor v Robin Montgomery | 3-6,3-6 | |
| WTA Limoges | 12/14 18:05 | 25 | [375] Robin Montgomery v Polona Hercog [134] | 6-4,4-6,4-6 | |
| US Open - Kobiety | 08/25 18:05 | 14 | [354] Robin Montgomery v Jodie Anna Burrage [235] | 4-6,1-6 | |
| WTA San Jose | 08/01 22:05 | 19 | [118] Ana Konjuh v Robin Montgomery [357] | 6-3,7-6 | |
| WTA San Jose | 07/31 22:20 | 14 | [357] Robin Montgomery v Arina Rodionova [155] | 6-4,6-0 | |
| ITF - Evansville W25 | 07/15 14:00 | 26 | [368] Robin Montgomery v Catherine Harrison [315] | 3-6,6-7 | |
| ITF - Evansville W25 | 07/14 16:40 | 25 | [278] Victoria Rodriguez v Robin Montgomery [368] | 6-2,2-6,2-6 | |
| ITF - Bonita Springs W100 | 05/12 19:00 | 25 | [81] Madison Brengle v Robin Montgomery [353] | 6-2,6-2 | |
| WTA Miami | 03/23 15:00 | 23 | [50] Magda Linette v Robin Montgomery [368] | 6-1,3-6,6-0 | |
| ITF - Boca Raton W25 | 02/25 18:05 | 26 | [373] Robin Montgomery v Hailey Baptiste [242] | 3-6,3-6 | |
| ITF - Boca Raton W25 | 02/24 18:45 | 25 | [373] Robin Montgomery v Jovana Jovic [248] | 6-1,6-1 | |
| ITF - Orlando W25 | 02/17 15:00 | 25 | [31] Amanda Anisimova v Robin Montgomery [368] | 6-7,6-4,6-3 | |
| ITF - Rome, GA W60 | 01/29 16:00 | 27 | [413] Robin Montgomery v Irene Burillo Escorihuela [331] | 6-3,3-6,3-6 | |
| ITF - Rome, GA W60 | 01/28 16:55 | 26 | [186] Maria C O Serrano v Robin Montgomery [413] | 4-6,3-6 | |
| ITF - Rome, GA W60 | 01/27 20:35 | 25 | [458] Tara Moore v Robin Montgomery [413] | 3-6,0-6 | |
| ITF - Rome, GA W60 | 01/26 16:30 | 54 | [154] Erin Routliffe v Robin Montgomery [413] | 1-6,3-6 | |
| ITF - Rome, GA W60 | 01/25 18:30 | 54 | Katarina Jokic v Robin Montgomery | 6-4,3-6,7-10 | |
| ITF - Orlando W25 | 11/15 14:50 | 29 | [491] Robin Montgomery v Alycia Parks [364] | 6-3,4-6,2-6 | |
| ITF - Orlando W25 | 11/14 19:30 | 28 | [491] Robin Montgomery v Hanna Chang [302] | 7-6,6-2 | |
| ITF - Orlando W25 | 11/14 14:55 | 27 | Hurricane T Black v Robin Montgomery | 7-5,0-6,2-6 | |
| ITF - Orlando W25 | 11/13 14:50 | 26 | [491] Robin Montgomery v Tessah Andrianjafitrimo [253] | 7-5,6-4 |