Stadium: Court 6 Round: 54 Ground: Clay
| Plovdiv, Singles Qualifying M-ITF-BUL-03A | 2019/06/04 06:30 | Maiga, Riccardo v Michalis Sakellaridis | 6-2,6-0 |
| Reggio Emilia, Singles Qualifying M-ITF-ITA-11A | 2019/06/01 13:30 | Maiga, Riccardo v Andrea Guerrieri | 4-6,4-6 |
| Reggio Emilia, Singles Qualifying M-ITF-ITA-11A | 2019/06/01 09:00 | Maiga, Riccardo v Andrea Bolla | 3-6,6-3,11-9 |
| Reggio Emilia, Singles Qualifying M-ITF-ITA-11A | 2019/05/31 15:15 | Albertoni, Davide v Maiga, Riccardo | 4-6,2-6 |
| Reggio Emilia, Singles Qualifying M-ITF-ITA-11A | 2019/05/31 11:45 | Albertoni, Davide v Maiga, Riccardo | 4-6,2-6 |
| Reggio Emilia, Singles Qualifying M-ITF-ITA-11A | 2019/05/31 07:30 | Maiga, Riccardo v Virgili, Adelchi | 2-6,6-4,10-7 |
| Casale Monferrato, Singles M-ITF-ITA-09A | 2019/05/17 10:05 | Giovanni Fonio v Maiga, Riccardo | 7-6,6-4 |
| Casale Monferrato, Singles M-ITF-ITA-09A | 2019/05/16 10:00 | Battaglino, Stefano v Maiga, Riccardo | 6-7,1-6 |
| 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 Sozopol | 2019/05/09 07:00 | Milushev, Plamen v Kirkov, Vasil | 2-6,3-6 |
| ITF M15 Sozopol | 2019/05/07 10:00 | Milushev, Plamen v Dian Nedev | 6-2,6-2 |
| ITF Turkey F38 | 2018/11/25 07:00 | Nareyka, Bjorn v Milushev, Plamen | 0-6,6-7 |
| ITF Turkey F37 | 2018/11/22 08:10 | Katic, Dejan v Milushev, Plamen | 4-6,6-4,6-3 |
| ITF Turkey F37 | 2018/11/21 07:00 | Milushev, Plamen v Pointon, Samuel | 6-0,6-3 |
| ITF Turkey F37 | 2018/11/19 11:45 | Speziali, Maurizio v Milushev, Plamen | 5-7,3-6 |
| ITF Turkey F37 | 2018/11/19 06:30 | Milushev, Plamen v Voinea, Christian | 6-3,6-0 |