Stadium: Court 2 Round: 44 Ground: Hardcourt outdoor
| UTR Pro Tennis Series Sofia Women | 2021/09/03 10:00 | Amariei I Dalina v Tchakarova, Eleonore | 3-6,6-3,6-0 |
| UTR Pro Tennis Series Sofia Women | 2021/09/02 11:30 | Tchakarova, Eleonore v Maja Radenkovic | 6-2,6-3 |
| UTR Pro Tennis Series Sofia Women | 2021/09/01 06:30 | Tchakarova, Eleonore v Kraleva, Elena | 6-2,5-0 |
| UTR Pro Tennis Series Sofia Women | 2021/08/31 06:30 | Tchakarova, Eleonore v Mariya Poduraeva | 6-3,5-2 |
| UTR Pro Tennis Series Sofia Women | 2021/08/30 07:00 | Tchakarova, Eleonore v Julia Terziyska | 0-6,3-6 |
| ITF W60 Prerov | 2021/08/22 08:00 | Jessie Aney v Tchakarova, Eleonore | 6-1,6-0 |
| ITF W25 Vrnjacka Banja | 2021/08/16 08:00 | Veronika Erjavec v Tchakarova, Eleonore | 6-1,6-1 |
| ITF W25 Vrnjacka Banja | 2021/08/15 07:00 | Gvozdenovic, Sara v Tchakarova, Eleonore | 1-6,2-6 |
| ITF Women Varna | 2021/09/05 07:00 | Peruhova, Lyuboslava v Eleni Christofi | 1-6,0-6 |
| ITF - W15 Antalya | 2019/12/16 06:30 | Csabi, Petra v Peruhova, Lyuboslava | 2-6,6-0,10-7 |
| Antalya, Qualifications Simples W-ITF-TUR-35A | 2019/12/08 09:30 | Peruhova, Lyuboslava v Olivia Gram | 0-6,0-6 |
| ITF - W15 Antalya | 2019/12/02 07:00 | Peruhova, Lyuboslava v Meers, Luna | 1-6,3-6 |
| ITF - W15 Héraklion | 2019/11/18 08:00 | Celia Cervino Ruiz v Peruhova, Lyuboslava | 6-3,6-1 |
| ITF - W15 Héraklion | 2019/11/17 07:30 | Peruhova, Lyuboslava v Ortega Redondo, Paula | 7-5,1-6,10-6 |
| ITF - W15 Héraklion | 2019/11/11 08:00 | Duca, Gabriela v Peruhova, Lyuboslava | 6-4,6-2 |
| ITF - W15 Héraklion | 2019/11/03 09:30 | Peruhova, Lyuboslava v Koldobski, Koral | 1-6,2-6 |