Round: 54 Ground: Clay
| ITF Women Dobrich | 2016/09/13 11:25 | Brouleau, Lou v Magdalena Stoilkovska | 6-4,6-0 |
| Sofia, Singles W-WITF-BUL-01A | 2016/09/06 07:30 | Stokke, Melanie v Magdalena Stoilkovska | 6-1,6-1 |
| ITF Women St. Poelten | 2016/08/30 12:15 | Sumova, Diana v Magdalena Stoilkovska | 6-3,6-2 |
| ITF Women St. Poelten | 2016/08/27 12:00 | Magdalena Stoilkovska v Schwarte, Emelie | 7-5,6-2 |
| Billie Jean King Cup | 2016/04/16 09:15 | Magdalena Stoilkovska v Ulrikke Eikeri | 3-6,4-6 |
| Billie Jean King Cup | 2016/04/13 10:10 | Drummy, Georgia v Magdalena Stoilkovska | 6-3,5-7,4-6 |
| Billie Jean King Cup | 2016/04/12 09:15 | Amiraghyan, Ani v Magdalena Stoilkovska | 6-0,6-2 |
| ITF USA F31 MD | 2016/10/09 11:00 | Bosch, Maria Virginia v Montero, Milagros | 0-6,2-6 |
| ITF Women Hammamet | 2016/10/05 08:30 | Sella, Francesca v Montero, Milagros | 6-3,6-1 |
| Hammamet, Singles Qualifying W-WITF-TUN-20A | 2016/09/26 09:30 | Montero, Milagros v Genovese, Elaine | 0-6,1-6 |