Stadium: Court 2 Round: 25 Ground: Hardcourt outdoor
| UTR Pro Tennis Series Pazardzhik Women | 2021/05/08 09:00 | Gebriela Mihaylova v Ani Vangelova | 2-6,5-7 |
| ITF Women Sozopol | 2016/09/27 22:00 | Gebriela Mihaylova v Ani Vangelova | 4-6,2-6 |
| ITF W15 Sozopol | 2021/09/14 09:00 | Denislava Glushkova v Gebriela Mihaylova | 6-1,6-3 |
| ITF W15 Varna | 2021/09/09 10:25 | Martha Matoula v Gebriela Mihaylova | 6-3,6-1 |
| ITF W15 Varna | 2021/09/07 06:30 | Margarita Ignatjeva v Gebriela Mihaylova | 4-6,6-7 |
| ITF W15 Prokuplje | 2021/07/06 07:00 | Karola Bejenaru v Gebriela Mihaylova | 6-4,6-1 |
| ITF W15 Prokuplje | 2021/07/04 07:00 | Graziella Barrett v Gebriela Mihaylova | 0-6,0-6 |
| ITF W15 Prokuplje | 2021/06/27 11:00 | Gebriela Mihaylova v Noka Juric | 4-6,3-6 |
| ITF W15 Antalya | 2021/06/08 07:00 | Gebriela Mihaylova v Daria Shalamanova | 6-3,3-6,11-13 |
| ITF W15 Antalya | 2021/06/02 07:20 | Basak Eraydin v Gebriela Mihaylova | 6-4,6-2 |
| ITF W15 Sozopol | 2021/09/14 10:00 | Vanessa Ersoz v Ani Vangelova | 6-4,6-2 |
| ITF W15 Varna | 2021/09/09 06:30 | Jana Bojovic v Ani Vangelova | 6-2,6-1 |
| ITF W15 Varna | 2021/09/08 06:30 | Ani Vangelova v Ilay Yoruk | 6-4,3-6,6-2 |
| ITF W25 Marbella | 2021/08/30 09:30 | Mia Mack v Ani Vangelova | 7-6,6-7,10-5 |
| ITF W25 Vigo | 2021/08/24 08:00 | Jacqueline Cabaj Awad v Ani Vangelova | 6-3,6-3 |
| ITF W25 Vigo | 2021/08/23 08:00 | Nina Ugrelidze v Ani Vangelova | 2-6,4-6 |
| ITF W60 San Bartolome De Tirajana | 2021/08/15 08:30 | Ani Vangelova v Karola Bejenaru | 2-6,1-6 |
| ITF W60 San Bartolome De Tirajana | 2021/08/09 10:35 | Yvonne Cavalle-Reimers v Ani Vangelova | 6-0,6-2 |