| WTA Miami | 03/22 16:55 | 23 | [193] Robin Montgomery v Ana Bogdan [60] | 3-6,6-3,6-3 | |
| WTA Indian Wells | 03/06 19:00 | 14 | [187] Robin Montgomery v Magdalena Frech [106] | 6-7,3-6 | |
| WTA Austin | 03/01 00:55 | 25 | [189] Robin Montgomery v Coco Vandeweghe [136] | 2-6,7-6,6-7 | |
| WTA Austin | 02/26 16:30 | 19 | [193] Robin Montgomery v Elvina Kalieva [234] | 7-6,6-1 | |
| WTA Austin | 02/25 17:05 | 45 | [131] Jodie Anna Burrage v Robin Montgomery [193] | 4-6,5-7 | |
| ITF W60 Orlando | 02/07 18:30 | 25 | [192] Robin Montgomery v Elizabeth Mandlik [153] | 5-7,6-4,4-6 | |
| ITF W60 Rome, GA | 02/02 16:00 | 26 | [212] Robin Montgomery v Ashley Lahey [348] | 3-6,6-1,3-6 | |
| ITF W60 Rome, GA | 02/01 17:30 | 25 | [189] Kayla Day v Robin Montgomery [212] | 6-7,6-7 | |
| ITF W25 Orlando | 01/29 15:50 | 29 | [209] Peyton Stearns v Robin Montgomery [218] | 6-2,6-0 | |
| ITF W25 Orlando | 01/28 15:00 | 28 | [218] Robin Montgomery v Ann Li [168] | 6-4,2-6,6-3 | |
| ITF W25 Orlando | 01/27 14:50 | 27 | Robin Montgomery v Victoria Hu | 6-2,7-5 | |
| ITF W25 Orlando | 01/26 15:00 | 26 | [218] Robin Montgomery v Rina Saigo [425] | 6-3,6-4 | |
| ITF W25 Orlando | 01/25 17:30 | 25 | Robin Montgomery v Irina Falconi | 7-6,6-3 | |
| Ausztrál Open - nők | 01/11 06:25 | 15 | [105] Diana Shnaider v Robin Montgomery [218] | 6-4,6-4 | |
| Ausztrál Open - nők | 01/10 06:15 | 14 | [147] Maria Carle v Robin Montgomery [218] | 2-6,6-7 | |
| ITF W60 Canberra | 12/31 23:00 | 54 | [183] Ashlyn Krueger v Robin Montgomery [219] | 6-4,7-5 | |
| ITF W60 Calgary | 11/13 19:55 | 29 | [247] Robin Montgomery v Urszula Radwanska [420] | 7-6,7-5 | |
| ITF W60 Calgary | 11/12 22:00 | 28 | [265] Jamie Loeb v Robin Montgomery [247] | 4-6,6-1,6-7 | |
| ITF W60 Calgary | 11/12 01:00 | 27 | [427] Sabine Lisicki v Robin Montgomery [247] | 6-7,6-7 | |
| ITF W60 Calgary | 11/10 20:25 | 26 | Mia Kupres v Robin Montgomery | 3-6,6-7 | |
| ITF W60 Calgary | 11/08 17:00 | 25 | [171] Ji-Hee Choi v Robin Montgomery [247] | 3-6,1-6 | |
| WTA Midland | 11/01 14:00 | 25 | [257] Robin Montgomery v Katherine Sebov [229] | 6-7,7-5,3-6 | |
| WTA Midland | 10/31 15:30 | 19 | [186] Diana Shnaider v Robin Montgomery [257] | 3-6,2-6 | |
| WTA Midland | 10/30 19:05 | 14 | [354] Michaela Bayerlova v Robin Montgomery [263] | 2-6,1-6 | |
| ITF W60 Toronto | 10/28 16:05 | 27 | [465] Urszula Radwanska v Robin Montgomery [263] | 7-6,6-4 | |
| ITF W60 Toronto | 10/27 14:50 | 26 | Olivia Lincer v Robin Montgomery | 4-6,2-6 | |
| ITF W60 Toronto | 10/26 16:15 | 25 | [263] Robin Montgomery v Arianne Hartono [193] | 6-0,6-0 | |
| WTA San Diego | 10/12 02:50 | 25 | [294] Robin Montgomery v Cori Gauff [8] | 3-6,3-6 | |
| WTA San Diego | 10/09 21:20 | 19 | [297] Robin Montgomery v Bernarda Pera [43] | 1-6,6-1,6-4 | |
| WTA San Diego | 10/08 22:55 | 14 | [27] Shuai Zhang v Robin Montgomery [297] | 2-6,3-6 |