Stadium: Court 10 Round: 25 Ground: Clay
| ITF M25 Kramsach | 2023/07/26 10:00 | Sebastian Prechtel v Milos Karol | 7-5,7-6 |
| ITF M25 Telfs | 2023/07/20 10:35 | Milos Karol v Sandro Kopp | 3-6,3-6 |
| ITF M25 Telfs | 2023/07/19 12:20 | Gustaf Strom v Milos Karol | 6-7,3-6 |
| Challenger Salzburg | 2023/07/09 10:10 | Milos Karol v Vladyslav Orlov | 7-5,3-6,1-6 |
| ITF M25 Poprad | 2023/06/22 08:00 | Lukas Palovic v Milos Karol | 2-6,6-3,6-4 |
| ITF M25 Poprad | 2023/06/21 09:55 | Milos Karol v Alibek Kachmazov | 7-5,6-4 |
| Challenger Bratislava | 2023/06/12 15:00 | Vitaliy Sachko v Milos Karol | 6-4,6-1 |
| Challenger Bratislava | 2023/06/11 15:15 | Milos Karol v Ulises Blanch | 4-6,7-6,6-4 |
| ITF M25 The Hague | 2023/07/06 12:10 | Eric Vanshelboim v Olaf Pieczkowski | 6-0,6-4 |
| ITF M25 The Hague | 2023/07/04 12:40 | Dax Donders v Olaf Pieczkowski | 6-7,6-4,2-6 |
| ITF M15 Wroclaw | 2023/06/29 08:00 | Kirill Kivattsev v Olaf Pieczkowski | 4-6,6-0,6-1 |
| ITF M15 Wroclaw | 2023/06/28 13:05 | Olaf Pieczkowski v Filip Duda | 6-2,6-2 |
| ITF M25 Poprad | 2023/06/21 09:50 | Olaf Pieczkowski v Toby Alex Kodat | 0-6,1-6 |
| ITF M15 Litija | 2023/06/15 12:45 | Luca Wiedenmann v Olaf Pieczkowski | 6-3,6-0 |
| ITF M15 Litija | 2023/06/14 12:10 | Nikola Basic v Olaf Pieczkowski | 0-6,2-6 |
| ITF M15 Constanta | 2023/06/01 08:00 | Radu Mihai Papoe v Olaf Pieczkowski | 6-1,6-4 |