Stadium: Court 1 Round: 54 Ground: Clay
| ITF W15 Prokuplje | 2019/07/08 09:30 | Milenkovic, Kristina v Ayari, Mey | 6-1,6-0 |
| ITF W25 Stuttgart | 2019/07/02 08:00 | Iva Primorac v Milenkovic, Kristina | 6-1,7-5 |
| ITF W25 Stuttgart | 2019/07/01 09:25 | Milenkovic, Kristina v Fomina, Alona | 7-6,6-2 |
| ITF W25 Darmstadt | 2019/06/24 08:00 | Jule Niemeier v Milenkovic, Kristina | 6-3,6-3 |
| ITF W60 Stare Splavy | 2019/06/17 10:55 | Milenkovic, Kristina v Nikola Tomanova | 4-6,2-6 |
| ITF - W15 Antalya | 2019/04/10 08:55 | Milenkovic, Kristina v Kubanova, Karolina | 6-7,5-7 |
| ITF - W15 Antalya | 2019/04/09 09:30 | Milenkovic, Kristina v Rittberger, Annika Chiara | 6-1,6-1 |
| ITF - W15 Antalya | 2019/04/08 07:15 | Milenkovic, Kristina v Danilchenko, Anfisa | 6-1,6-1 |
| ITF W15 Prokuplje | 2019/07/08 07:00 | Bajagic, Tamara v Joksovic, Doroteja | 1-6,2-6 |
| ITF W15 Prokuplje | 2019/07/03 10:15 | Joksovic, Doroteja v Jocovic, Andjela | 1-6,6-2,6-7 |
| ITF W15 Prokuplje | 2019/07/02 07:00 | Ukolova, Anna v Joksovic, Doroteja | 2-6,0-6 |
| ITF W15 Prokuplje | 2019/07/01 07:00 | Poile, Miranda v Joksovic, Doroteja | 3-6,2-6 |
| Tabarka, Singles W-ITF-TUN-18A | 2019/06/27 10:25 | Joksovic, Doroteja v Nuria Brancaccio | 4-6,2-6 |
| Tabarka, Singles W-ITF-TUN-18A | 2019/06/25 09:25 | Giorgia Pinto v Joksovic, Doroteja | 4-6,3-6 |
| Tabarka, Singles W-ITF-TUN-18A | 2019/06/24 14:00 | Joksovic, Doroteja v Carola Cavelli | 6-1,6-0 |
| Tabarka, Singles W-ITF-TUN-18A | 2019/06/19 10:45 | Joksovic, Doroteja v Julieta Lara Estable | 1-6,3-6 |