Stadium: Center Court Round: 26 Ground: Clay
| ITF M25 Bielsko Biala | 2023/08/16 09:00 | Ondrej Horak v Olaf Pieczkowski | 6-3,1-6,0-6 |
| ITF M25 Lodz | 2023/08/10 10:30 | Daniel Paty v Olaf Pieczkowski | 6-3,6-2 |
| ITF M25 Lodz | 2023/08/09 09:20 | Milos Karol v Olaf Pieczkowski | 6-3,2-6,3-6 |
| ITF M25 Hága | 2023/07/06 12:10 | Eric Vanshelboim v Olaf Pieczkowski | 6-0,6-4 |
| ITF M25 Hága | 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 M25 Bielsko Biala | 2023/08/16 11:35 | Daniel Siniakov v Yshai Oliel | 6-3,2-6,7-5 |
| Challenger Liberec | 2023/07/30 12:35 | Alex M Pujolras v Daniel Siniakov | 1-6,6-3,6-1 |
| ITF M25 Telfs | 2023/07/21 12:00 | Peter Heller v Daniel Siniakov | 6-1,6-0 |
| ITF M25 Telfs | 2023/07/20 08:30 | Daniel Siniakov v Juan Bautista Otegui | 2-6,6-3,6-3 |
| ITF M25 Telfs | 2023/07/19 10:00 | Daniel Siniakov v Timofey Stepanov | 4-6,6-3,6-0 |
| ITF M25 Kassel | 2023/07/12 11:25 | Daniel Siniakov v Facundo Yunis | 4-6,1-6 |
| ITF M25 Kassel | 2023/07/11 09:30 | Daniel Siniakov v Taym Alazmeh | 6-3,7-6 |
| ITF M25 Kassel | 2023/07/10 08:00 | Daniel Siniakov v Vojtech Mares | 7-5,6-4 |