Stadium: Court 3 Round: 25 Ground: Hardcourt outdoor
| Challenger Milan | 2019/06/24 15:50 | Raul Brancaccio v Julian Ocleppo | 1-6,6-3,5-7 |
| Challenger Parma | 2019/06/17 16:00 | Andrea Pellegrino v Julian Ocleppo | 6-4,6-0 |
| Challenger Vicenza | 2019/05/30 16:50 | Julian Ocleppo v Gianluca Mager | 4-6,7-5,6-7 |
| Challenger Vicenza | 2019/05/28 09:40 | Kenny de Schepper v Julian Ocleppo | 0-6,4-6 |
| Challenger Jerusalem | 2019/05/22 10:25 | Julian Ocleppo v John-Patrick Smith | 6-7,5-7 |
| Challenger Jerusalem | 2019/05/21 08:25 | Yshai Oliel v Julian Ocleppo | 6-7,2-6 |
| Challenger Jerusalem | 2019/05/20 07:00 | Julian Ocleppo v Yair Sarouk | 6-1,6-4 |
| Challenger Rome | 2019/05/06 15:00 | Mate Valkusz v Julian Ocleppo | 6-2,6-2 |
| ITF M15 Irpin | 2019/05/27 10:00 | Vladyslav Gorodynskyi v Piotr Matuszewski | 2-6,7-6,15-13 |
| ITF M15 Irpin | 2019/05/27 06:30 | Demian Hulyanich v Piotr Matuszewski | 3-6,2-6 |
| ITF M15 Tbilisi | 2019/05/01 11:00 | Piotr Matuszewski v Peter Bothwell | 7-6,1-6,4-6 |
| ITF M15 Tbilisi | 2019/04/30 06:00 | Piotr Matuszewski v Mikel Martinez | 6-3,6-4 |
| ITF M15 Sharm El Sheikh | 2019/04/11 08:00 | Daniel Michalski v Piotr Matuszewski | 6-2,6-1 |
| ITF M15 Sharm El Sheikh | 2019/04/10 08:00 | Piotr Matuszewski v Timur Kiyamov | 6-4,6-7,7-6 |
| ITF M15 Sharm El Sheikh | 2019/04/09 09:45 | Piotr Matuszewski v Marius Ruzgas | 7-6,6-3 |
| ITF M15 Oslo | 2019/03/05 09:00 | Bart Stevens v Piotr Matuszewski | 2-6,6-1,10-8 |