Stadium: Court 17 Round: 25 Ground: Clay
| ITF - W25 Orlando | 2021/02/17 15:00 | Amanda Anisimova v Robin Montgomery | 6-7,6-4,6-3 |
| ITF - W60 Rome, GA | 2021/01/29 16:00 | Robin Montgomery v Irene Burillo Escorihuela | 6-3,3-6,3-6 |
| ITF - W60 Rome, GA | 2021/01/28 16:55 | Maria Camila Osorio v Robin Montgomery | 4-6,3-6 |
| ITF - W60 Rome, GA | 2021/01/27 20:35 | Tara Moore v Robin Montgomery | 3-6,0-6 |
| ITF - W60 Rome, GA | 2021/01/26 16:30 | Erin Routliffe v Robin Montgomery | 1-6,3-6 |
| ITF - W60 Rome, GA | 2021/01/25 18:30 | Katarina Jokic v Robin Montgomery | 6-4,3-6,7-10 |
| ITF - W25 Orlando | 2020/11/15 14:50 | Robin Montgomery v Alycia Parks | 6-3,4-6,2-6 |
| ITF - W25 Orlando | 2020/11/14 19:30 | Robin Montgomery v Hanna Chang | 7-6,6-2 |
| ITF - W25 Orlando | 2021/02/18 14:45 | Jovana Jovic v Anhelina Kalinina | 2-6,3-6 |
| ITF - W25 Orlando | 2021/02/17 17:30 | Sophia Whittle v Jovana Jovic | 6-3,3-6,1-6 |
| ITF - W60 Rome, GA | 2021/01/27 17:00 | Maria Camila Osorio v Jovana Jovic | 7-5,6-4 |
| Australian Open - Kvinder | 2021/01/10 08:50 | Jia-Jing Lu v Jovana Jovic | 6-1,6-2 |
| ITF W80 - Macon | 2020/10/19 18:45 | Ankita Raina v Jovana Jovic | 6-1,3-6,10-1 |
| French Open - Kvinder | 2020/09/22 09:55 | Ankita Raina v Jovana Jovic | 6-4,4-6,6-4 |
| ITF W25 - Frydek Mistek | 2020/09/16 09:25 | Jesika Maleckova v Jovana Jovic | 6-1,6-2 |
| ITF W25 - Prag | 2020/09/08 09:35 | Jovana Jovic v Miriam Kolodziejova | 6-7,1-6 |