Stadium: Court 22 Round: 62 Ground: Clay
| ITF - M15 Héraklion | 2019/12/01 09:00 | Dimitrov, Martin v Domagoj Biljesko | 3-6,1-6 |
| ITF - M15 Héraklion | 2019/11/26 08:00 | Dimitrov, Martin v Martinez, Alex | 5-7,6-4,8-10 |
| ITF - M15 Héraklion | 2019/11/25 09:00 | Lebedev, Alexander v Dimitrov, Martin | 1-6,6-7 |
| ITF - M15 Héraklion | 2019/11/20 12:10 | Dimitrov, Martin v Hampel, Lenny | 1-6,1-6 |
| ITF - M15 Héraklion | 2019/11/19 07:30 | Kalender, Admir v Dimitrov, Martin | 3-6,1-6 |
| ITF - M15 Héraklion | 2019/11/18 08:00 | Kapiris, Stamatis v Dimitrov, Martin | 2-6,6-2,6-10 |
| ITF - M15 Héraklion | 2019/11/17 07:30 | Dimitrov, Martin v Uryson, Nicolas | 6-3,6-3 |
| ITF - M15 Héraklion | 2019/11/11 08:00 | Dimitrov, Martin v Moroni, Filippo | 4-6,4-6 |