Stadium: Court 5 Round: 45 Ground: Clay
| ITF W25 Verbier | 2021/08/22 09:10 | Matilde Paoletti v Mariia Kostiuk | 6-4,6-0 |
| ITF - W15 Antalya | 2021/03/17 10:55 | Detiuc, Anastasia v Matilde Paoletti | 3-6,6-3,6-3 |
| ITF - W15 Antalya | 2021/03/10 11:20 | Gergana Topalova v Matilde Paoletti | 3-6,6-1,6-2 |
| ITF - W15 Antalya | 2021/02/12 10:30 | Custic, Marta v Matilde Paoletti | 7-5,5-7,6-2 |
| ITF - W15 Antalya | 2021/02/11 09:15 | Matilde Paoletti v Koval, Vlada | 6-4,7-5 |
| ITF - W15 Antalya | 2021/02/09 13:50 | Matilde Paoletti v Samudio, Antonia | 6-3,6-0 |
| ITF - W15 Antalya | 2021/02/04 06:30 | Sapfo Sakellaridi v Matilde Paoletti | 6-4,6-2 |
| ITF - W15 Antalya | 2021/02/03 11:35 | Matilde Paoletti v Nuria Brancaccio | 6-1,7-6 |
| ITF W25 Verbier | 2021/08/22 09:25 | Naima Karamoko v Milenkovic, Kristina | 6-7,5-7 |
| ITF W25 Telavi | 2021/07/19 08:45 | Martina Spigarelli v Milenkovic, Kristina | 6-3,6-3 |
| ITF W25 Telavi | 2021/07/12 06:00 | Alexandra Osborne v Milenkovic, Kristina | 6-2,6-4 |
| ITF W25 Telavi | 2021/07/11 06:30 | Anamaria Kurtsikashvili v Milenkovic, Kristina | 6-4,0-6,5-10 |
| ITF W15 Prokuplje | 2021/07/05 09:45 | Bertoloni, Anita v Milenkovic, Kristina | 6-1,6-3 |
| ITF W15 Prokuplje | 2021/07/04 09:30 | Milenkovic, Kristina v Gemovic, Elena | 6-1,6-2 |
| ITF W15 Prokuplje | 2021/06/28 11:30 | Karola Patricia Bejenaru v Milenkovic, Kristina | 2-6,6-1,10-8 |
| ITF W25 Klosters | 2021/06/21 11:00 | Alexandra Vecic v Milenkovic, Kristina | 6-3,6-3 |