Stadium: Court 5 Round: 25 Ground: Hardcourt outdoor
| ITF W25 Salinas | 2021/05/04 14:00 | Tchakarova, Eleonore v Lia Karatancheva | 5-7,1-6 |
| ITF W15 Cancun | 2021/12/07 18:00 | Yuliana Monroy v Lia Karatancheva | 6-1,6-2 |
| ITF W15 Cancun | 2021/12/04 19:10 | Hina Inoue v Lia Karatancheva | 6-2,6-4 |
| ITF W15 Cancun | 2021/11/30 21:50 | Lia Karatancheva v Maria Camila Torres Murcia | 6-4,6-0 |
| ITF W15 Cancun | 2021/11/24 16:20 | Lia Karatancheva v Leclercq, Anaelle | 5-7,6-1,2-6 |
| ITF W25 Naples | 2021/11/16 15:55 | Lia Karatancheva v Tilbuerger, Jantje | 5-7,6-7 |
| ITF W25 Naples | 2021/11/15 15:30 | Dia Evtimova v Lia Karatancheva | 1-6,1-6 |
| ITF W25 Daytona Beach | 2021/11/09 16:40 | Tilbuerger, Jantje v Lia Karatancheva | 6-1,6-7,11-9 |
| ITF W25 Daytona Beach | 2021/11/08 16:00 | Lia Karatancheva v Adriana Reami | 3-6,6-4,10-6 |
| ITF W15 Cancun | 2021/12/07 21:10 | Tchakarova, Eleonore v Jessica Hinojosa Gomez | 2-6,3-6 |
| UTR Pro Tennis Series Florida Women | 2021/11/07 13:30 | Sysoeva, Anastasia v Tchakarova, Eleonore | 4-6,1-4 |
| UTR Pro Tennis Series Florida Women | 2021/11/06 15:30 | Tchakarova, Eleonore v Wijesundera, Rushri | 7-6,6-3 |
| UTR Pro Tennis Series Florida Women | 2021/11/05 14:30 | Ariana Pursoo v Tchakarova, Eleonore | 6-2,5-0 |
| UTR Pro Tennis Series Florida Women | 2021/11/04 15:00 | Meisha Kendall-Woseley v Tchakarova, Eleonore | 2-6,5-7 |
| UTR Pro Tennis Series Florida Women | 2021/11/02 17:00 | Madison Bourguignon v Tchakarova, Eleonore | 4-5 |
| UTR Pro Tennis Series Florida Women | 2021/11/01 13:00 | Tchakarova, Eleonore v Tchakarova, Verginie | 7-5,6-4 |
| ITF W15 Cancun | 2021/10/14 18:10 | Darja Semenistaja v Tchakarova, Eleonore | 6-2,6-2 |