| 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 | |
| USA lahtised meistrivõistlused - naised | 08/29 22:10 | 23 | [147] Robin Montgomery v Eva Lys [143] | 2-6,1-6 | |
| WTA Stanford | 08/16 01:40 | 26 | [150] Robin Montgomery v Kamilla Rakhimova [80] | 5-7,3-6 | |
| WTA Stanford | 08/13 21:00 | 25 | [183] Coco Vandeweghe v Robin Montgomery [150] | 3-6,6-7 | |
| Wimbledon - naised | 06/28 16:45 | 15 | [121] Greet Minnen v Robin Montgomery [147] | 6-4,7-6 | |
| Wimbledon - naised | 06/27 13:30 | 14 | [147] Robin Montgomery v Magali Kempen [200] | 6-4,6-2 | |
| WTA Gaiba | 06/24 13:20 | 28 | [162] Robin Montgomery v Ashlyn Krueger [143] | 7-6,4-6,2-6 | |
| WTA Gaiba | 06/23 16:00 | 27 | [162] Robin Montgomery v Ysaline Bonaventure [93] | 6-4,6-2 | |
| WTA Gaiba | 06/22 14:20 | 26 | [162] Robin Montgomery v Laura Pigossi [133] | 6-0,6-7,6-0 | |
| WTA Gaiba | 06/20 13:40 | 25 | [105] Taylor Townsend v Robin Montgomery [162] | 6-4,4-6,6-7 | |
| ITF W60 Madrid | 06/16 08:05 | 27 | [284] Tatiana Prozorova v Robin Montgomery [167] | 6-7,7-5,6-4 | |
| ITF W60 Madrid | 06/15 07:30 | 26 | [278] Jana Kolodynska v Robin Montgomery [167] | 2-6,4-6 | |
| ITF W60 Madrid | 06/13 13:35 | 25 | Noelia Bouzo Zanotti v Robin Montgomery | 4-6,3-6 | |
| Prantsusmaa lahtised - naised | 05/23 09:25 | 14 | [166] Robin Montgomery v Aliona Bolsova [131] | 1-6,3-6 | |
| ITF W60 Saint-Gaudens | 05/21 08:30 | 29 | [195] Robin Montgomery v Alice Robbe [212] | 7-5,6-4 | |
| ITF W60 Saint-Gaudens | 05/20 11:00 | 28 | [195] Robin Montgomery v Nigina Abduraimova [181] | 7-5,6-3 | |
| ITF W60 Saint-Gaudens | 05/19 08:30 | 27 | [195] Robin Montgomery v Margaux Rouvroy [292] | 6-4,6-2 | |
| ITF W60 Saint-Gaudens | 05/18 08:00 | 26 | [195] Robin Montgomery v Carolina Alves [224] | 6-2,6-4 | |
| ITF W60 Saint-Gaudens | 05/17 07:55 | 25 | [195] Robin Montgomery v Maria F Herazo Gonzalez [398] | 6-3,2-6,6-0 | |
| ITF W100 Bonita Springs | 05/03 18:25 | 25 | [263] Astra Sharma v Robin Montgomery [181] | 1-6,7-5,7-6 | |
| ITF W60 Charlottesville | 04/26 18:10 | 25 | [181] Robin Montgomery v Emma Navarro [101] | 0-6,0-6 | |
| ITF W100 Charleston | 04/20 16:15 | 26 | [182] Robin Montgomery v Emma Navarro [121] | 3-6,2-6 | |
| ITF W100 Charleston | 04/19 20:20 | 25 | [377] Maria Mateas v Robin Montgomery [182] | 6-2,5-7,3-6 | |
| ITF W25 Boca Raton | 04/13 14:45 | 25 | Robin Montgomery v Yulia Starodubtsewa | 7-6,5-7,0-6 | |
| WTA Charleston | 04/01 15:45 | 14 | [193] Robin Montgomery v Ashlyn Krueger [155] | 2-6,6-7 | |
| WTA Miami | 03/24 18:35 | 24 | [193] Robin Montgomery v Madison Keys [21] | 4-6,4-6 |