Stadium: Court 18 Round: 62 Ground: Clay
| ITF - W15 Monastir | 2021/11/18 10:10 | Zhuoma Ni Ma v Milenkovic, Kristina | 2-6,1-6 |
| ITF - W15 Monastir | 2021/11/17 08:30 | Milenkovic, Kristina v Yu Shan | 6-3,6-4 |
| ITF - W15 Monastir | 2021/11/11 07:55 | Milenkovic, Kristina v Adithya Karunaratne | 1-6,0-6 |
| ITF - W15 Monastir | 2021/11/10 12:00 | Selya Rakki v Milenkovic, Kristina | 6-4,4-6,0-6 |
| ITF - W15 Monastir | 2021/10/20 11:25 | Elina Zakharova v Milenkovic, Kristina | 6-3,7-5 |
| ITF - W15 Monastir | 2021/10/14 11:30 | Milenkovic, Kristina v Mara Guth | 1-6,3-6 |
| ITF - W15 Monastir | 2021/10/12 10:30 | Milenkovic, Kristina v Arianna Nepomuceno | 6-1,7-5 |
| ITF W25 Jablonec nad Nisou | 2021/09/12 08:30 | Romana Cisovska v Milenkovic, Kristina | 6-1,4-6,10-5 |
| UTR Pro Tennis Series Bucharest Women | 2021/11/14 12:00 | Tsoneva, Mihaela v Bianca E Barbulescu | 3-6,1-6 |
| UTR Pro Tennis Series Bucharest Women | 2021/11/13 16:30 | Tsoneva, Mihaela v Bertea Ruxandra | 6-2,5-3 |
| UTR Pro Tennis Series Bucharest Women | 2021/11/12 08:30 | Stefana Lazar v Tsoneva, Mihaela | 1-6,6-7 |
| UTR Pro Tennis Series Bucharest Women | 2021/11/11 10:00 | Floriana Popovici v Tsoneva, Mihaela | 2-6,1-5 |
| UTR Pro Tennis Series Bucharest Women | 2021/11/09 10:00 | Sokovic, Nevena v Tsoneva, Mihaela | 4-6,6-6 |
| UTR Pro Tennis Series Bucharest Women | 2021/11/08 07:00 | Tsoneva, Mihaela v Gaspar-Ivan, Ioana | 3-6,3-5 |
| UTR Pro Tennis Series Burgas Women | 2021/10/30 08:00 | Julia Terziyska v Tsoneva, Mihaela | 6-1,6-1 |
| UTR Pro Tennis Series Burgas Women | 2021/10/29 08:00 | Tsoneva, Mihaela v Ani Vangelova | 7-5,6-2 |