| UTR Pro Pazardzhik | 07/08 09:55 | - | Kai-Luca Ampaw v Gabriel Matuszewski | 6-2,6-3 | |
| UTR Pro Pazardzhik | 07/07 06:00 | - | Gabriel Matuszewski v Dian Nedev | 1-6,3-6 | |
| UTR Pro Skopje | 06/29 08:05 | 29 | Samuel Rovai v Gabriel Matuszewski | 3-6,2-6 | |
| UTR Pro Skopje | 06/28 06:00 | 28 | Gabriel Matuszewski v Eqbal/Nenwani | 3-6,6-2,6-4 | |
| UTR Pro Skopje | 06/27 11:40 | - | Juan Sebastian Osorio v Gabriel Matuszewski | 4-6,5-7 | |
| UTR Pro Skopje | 06/26 11:00 | - | Oskar Jansson v Gabriel Matuszewski | 6-2,6-2 | |
| UTR Pro Skopje | 06/25 06:00 | - | Stefan Skobelev v Gabriel Matuszewski | 6-4,1-6,6-3 | |
| UTR Pro Skopje | 06/23 11:25 | - | Janos Fekete v Gabriel Matuszewski | 6-7,6-4,6-4 | |
| UTR Pro Skopje | 06/22 07:00 | 29 | Mihnea Maftei v Gabriel Matuszewski | 7-6,6-3 | |
| UTR Pro Skopje | 06/21 08:40 | 28 | Mateja Stefanovic v Gabriel Matuszewski | 4-6,2-6 | |
| UTR Pro Skopje | 06/20 11:35 | - | Gabriel Matuszewski v Hugo Magnusson | 3-6,6-3,4-6 | |
| UTR Pro Skopje | 06/18 12:30 | - | Gabriel Matuszewski v Kristof Minarik | 5-7,1-6 | |
| UTR Pro Skopje | 06/17 07:00 | - | Gabriel Matuszewski v Tadija Radovanovic | 2-6,3-6 | |
| UTR Pro Skopje | 06/16 07:00 | - | Robert Watzka v Gabriel Matuszewski | 6-3,4-6,6-0 | |
| UTR Pro Bucharest | 06/15 08:55 | 29 | Gheorghe Claudiu Schinteie v Gabriel Matuszewski | 4-6,7-6,6-1 | |
| UTR Pro Bucharest | 06/14 09:10 | 28 | Vasile Antonescu v Gabriel Matuszewski | 1-6,4-6 | |
| UTR Pro Bucharest | 06/13 09:30 | - | Gabriel Matuszewski v Traian Petrica | 3-6,6-2,6-2 | |
| UTR Pro Bucharest | 06/12 09:40 | - | Gabriel Matuszewski v Fuchs/Holzer | 2-6,0-6 | |
| UTR Pro Bucharest | 06/11 13:50 | - | Sabi Roi v Gabriel Matuszewski | 4-6,1-6 | |
| UTR Pro Bucharest | 06/10 12:15 | - | Dario Alexandru Ciobotaru v Gabriel Matuszewski | 6-4,6-4 | |
| UTR Pro Glifada | 06/08 07:35 | 29 | Gabriel Matuszewski v Bonzi/Reboul | 7-6,6-2 | |
| UTR Pro Glifada | 06/07 08:25 | 28 | Gabriel Matuszewski v Vladimir Holban | 6-0,6-1 | |
| UTR Pro Glifada | 06/06 06:00 | - | Roman Postolka v Gabriel Matuszewski | 6-3,7-6 | |
| UTR Pro Glifada | 06/05 09:15 | - | Theodoros Mitsakos v Gabriel Matuszewski | 7-6,6-2 | |
| UTR Pro Glifada | 06/04 13:15 | - | Jupiter/Placette v Gabriel Matuszewski | 5-7,5-7 | |
| UTR Pro Glifada | 06/02 07:45 | - | Christos Glavas v Gabriel Matuszewski | 1-6,3-6 | |
| ITF M25 Heraklion | 05/28 13:52 | - | Pavlos Tsitsipas v Gabriel Matuszewski | 6-2,1-6,7-6 | |
| ITF M25 Heraklion | 05/27 08:00 | - | Gabriel Matuszewski v Ben Weintraub | 4-6,6-0,1-0 | |
| ITF M15 Heraklion | 05/07 08:30 | - | Leonardo Cattaneo v Gabriel Matuszewski | 7-5,7-6 | |
| ITF M15 Antalya | 03/27 09:37 | - | Gabriel Matuszewski v Gabriele Piraino | 1-6,4-6 |