Estadio: Court 8 Round: 44 Ground: Clay
| ITF W15 Heraklion | 2019/11/17 07:30 | Dejana Milenkovic v Alessia B Ciuca | 2-6,4-6 |
| ITF W15 Heraklion | 2019/11/10 07:30 | Dejana Milenkovic v Enola Chiesa | 1-6,3-6 |
| ITF W15 Vrnjacka Banja | 2019/08/28 10:35 | Dejana Milenkovic v Bojana Klincov | 1-6,1-6 |
| ITF W15 Vrnjacka Banja | 2019/08/27 07:00 | Izabela Gabriela Novac v Dejana Milenkovic | 6-0,6-3 |
| ITF W15 Vrnjacka Banja | 2019/08/25 06:30 | Dejana Milenkovic v Natalie Augustinova | 6-3,6-2 |
| ITF W15 Monastir | 2019/02/26 10:20 | Dalila Spiteri v Dejana Milenkovic | 6-2,6-2 |
| ITF Monastir - Femenino | 2018/12/19 11:20 | Claudia Giovine v Dejana Milenkovic | 6-1,6-0 |
| ITF Monastir - Femenino | 2018/12/10 08:30 | Maelys Bougrat v Dejana Milenkovic | 6-2,6-0 |
| ITF W15 Sharm El Sheikh | 2019/10/14 09:30 | Angelika Shapovalova v Chiara Catini | 7-6,0-6,4-10 |
| ITF W15 Sharm El Sheikh | 2019/10/09 13:25 | Victoria Kalaitzis v Angelika Shapovalova | 6-1,6-2 |
| ITF W15 El Cairo | 2019/09/17 09:50 | Angelika Shapovalova v Chiara Bordo | 6-4,3-6,5-10 |
| ITF W15 El Cairo | 2019/09/16 10:30 | Daria Solovyeva v Angelika Shapovalova | 4-6,1-6 |
| ITF W15 El Cairo | 2019/09/11 12:45 | Angelika Shapovalova v Margarita Lazareva | 6-3,2-6,3-6 |