| WTA Rouen | 04/16 13:00 | 25 | [181] Robin Montgomery v Arantxa Rus [53] | 3-6,1-6 | |
| WTA Rouen | 04/14 12:25 | 19 | [142] Jessika Ponchet v Robin Montgomery [182] | 4-6,5-7 | |
| WTA Rouen | 04/13 18:45 | 14 | [252] Valeriya Strakhova v Robin Montgomery [182] | 1-6,1-6 | |
| WTA San Luis Potosí | 03/29 18:00 | 27 | [270] Francesca Jones v Robin Montgomery [183] | 6-1,2-6,6-4 | |
| WTA San Luis Potosí | 03/27 18:00 | 26 | [183] Robin Montgomery v Hailey Baptiste [96] | 6-4,6-1 | |
| WTA San Luis Potosí | 03/25 23:35 | 25 | [135] Astra Sharma v Robin Montgomery [183] | 3-6,4-6 | |
| WTA Miami | 03/17 18:30 | 14 | [87] Laura Siegemund v Robin Montgomery [199] | 6-0,6-0 | |
| WTA Indian Wells | 03/07 21:50 | 23 | [199] Robin Montgomery v Hailey Baptiste [105] | 2-6,6-4,1-6 | |
| WTA Indian Wells | 03/05 22:00 | 15 | [124] Storm Hunter v Robin Montgomery [199] | 6-3,3-6,4-6 | |
| WTA Indian Wells | 03/04 00:50 | 14 | [193] Robin Montgomery v Marina Bassols Ribera [107] | 6-4,6-4 | |
| WTA Puerto Vallarta | 02/24 02:45 | 27 | [114] Hailey Baptiste v Robin Montgomery [207] | 4-6,6-1,6-2 | |
| WTA Puerto Vallarta | 02/22 00:50 | 26 | [207] Robin Montgomery v Renata Zarazua [102] | 6-1,6-4 | |
| WTA Puerto Vallarta | 02/20 21:35 | 25 | [207] Robin Montgomery v Solana Sierra [164] | 6-1,7-5 | |
| WTA Puerto Vallarta | 02/19 18:00 | 14 | [207] Robin Montgomery v Elvina Kalieva [226] | 6-2,6-4 | |
| ITF W75 Rome (GA) | 02/02 18:05 | 27 | [177] McCartney Kessler v Robin Montgomery [198] | 7-6,6-3 | |
| ITF W75 Rome (GA) | 02/01 17:40 | 26 | [248] Louisa Chirico v Robin Montgomery [198] | 2-6,1-6 | |
| ITF W75 Rome (GA) | 01/30 18:45 | 25 | [402] Clervie Ngounoue v Robin Montgomery [198] | 5-7,4-6 | |
| ITF W75 Vero Beach | 01/24 17:00 | 25 | [389] Gabriela Lee v Robin Montgomery [194] | 6-2,6-0 | |
| ITF W35 Naples | 01/20 15:55 | 28 | [194] Robin Montgomery v Leonie Kung [425] | 3-6,6-1,5-7 | |
| ITF W35 Naples | 01/19 18:50 | 27 | [194] Robin Montgomery v Louisa Chirico [258] | 3-6,7-6,6-4 | |
| ITF W35 Naples | 01/18 17:40 | 26 | Robin Montgomery v Akasha Urhobo | 6-4,6-4 | |
| ITF W35 Naples | 01/16 18:55 | 25 | Robin Montgomery v Malkia Ngounoue | 6-2,7-5 | |
| WTA Montevideo | 12/09 23:05 | 28 | [94] Diane Parry v Robin Montgomery [218] | 7-6,6-3 | |
| WTA Montevideo | 12/08 22:00 | 27 | [218] Robin Montgomery v Ylena In-Albon [275] | 6-2,6-1 | |
| WTA Montevideo | 12/06 20:05 | 26 | [157] Martina Capurro Taborda v Robin Montgomery [218] | 1-6,3-6 | |
| WTA Montevideo | 12/05 15:00 | 25 | [301] Leyre Romero Gormaz v Robin Montgomery [218] | 6-7,3-6 | |
| WTA Buenos Aires | 11/30 15:00 | 26 | [209] Solana Sierra v Robin Montgomery [224] | 6-4,7-5 | |
| WTA Buenos Aires | 11/28 16:55 | 25 | [224] Robin Montgomery v Sara Errani [104] | 6-3,6-4 | |
| WTA Guadalajara | 09/18 17:00 | 24 | [147] Robin Montgomery v Victoria Azarenka [23] | 1-6,1-6 | |
| US Open - Femenino | 08/29 22:10 | 23 | [147] Robin Montgomery v Eva Lys [143] | 2-6,1-6 |