Stadium: Court 1 Round: 25 Ground: Clay
| Piombino, Singles M-ITF-ITA-19A | 2019/08/28 19:10 | Bessire, Francesco v Griffith, William | 3-6,6-7 |
| Minsk, Singles M-ITF-BLR-01A | 2019/08/21 11:05 | Tsivadze, George v Bessire, Francesco | 6-1,6-3 |
| Irpin, Singles Qualifying M-ITF-UKR-04A | 2019/08/13 08:45 | Smirnov, Artem v Bessire, Francesco | 6-2,7-5 |
| Agadir, Singles Qualifying M-ITF-MAR-03A | 2019/07/31 12:45 | Bessire, Francesco v Moundir, Adam | 6-2,4-6,2-6 |
| ITF M15 Casablanca | 2019/07/22 09:00 | Bessire, Francesco v Smits, Glenn | 4-6,4-6 |
| Tanger, Singles M-ITF-MAR-01A | 2019/07/15 09:00 | Bessire, Francesco v Adnaoui, Mohamed | 6-4,3-6,9-11 |
| ITF M25 Casinalbo | 2019/07/08 13:00 | Cornea, Vlad Victor v Bessire, Francesco | 6-4,6-2 |
| ITF M25 Casinalbo | 2019/07/08 07:00 | Bettini, Filippo v Bessire, Francesco | 6-7,4-6,10-6 |
| Varna, Singles M-ITF-BUL-04A | 2019/09/09 10:00 | Grozdanov, Tihomir v Dimitrov, Martin | 4-6,5-7 |
| Targu Mures, Singles M-ITF-ROU-05A | 2019/08/06 09:35 | Melnic, Vladislav v Dimitrov, Martin | 6-4,6-1 |
| Targu Mures, Singles M-ITF-ROU-05A | 2019/08/05 08:00 | Savin, Robert Damian v Dimitrov, Martin | 3-6,1-6 |
| Chitila, Singles M-ITF-ROU-06A | 2019/07/30 12:20 | Solberg, Christoffer v Dimitrov, Martin | 6-4,1-6,11-9 |
| Chitila, Singles M-ITF-ROU-06A | 2019/07/30 06:30 | Borsan, Doru Junior v Dimitrov, Martin | 3-6,1-6 |
| Plovdiv, Singles Qualifying M-ITF-BUL-03A | 2019/06/04 06:30 | Dimitrov, Martin v Milushev, Plamen | 6-0,5-7,9-11 |
| ITF - M15 Héraklion | 2019/05/29 07:00 | Dimitrov, Martin v Crepaldi, Erik | 5-7,4-6 |
| ITF - M15 Héraklion | 2019/05/28 07:00 | Krainer, L. v Dimitrov, Martin | 4-6,4-6 |