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