Stadium: Court 15 Round: 26 Ground: Hardcourt outdoor
| ITF M15 Heraklion | 2023/10/18 06:30 | David Quayle v Oliver Ojakaar | 3-6,3-6 |
| ITF M25 Falun | 2023/09/25 07:50 | Johannes Ingildsen v Oliver Ojakaar | 6-2,6-2 |
| ITF M25 Falun | 2023/09/24 08:00 | Filip Stidell v Oliver Ojakaar | 1-6,2-6 |
| ITF M15 Danderyd | 2023/09/20 12:25 | Oliver Ojakaar v Mats Rosenkranz | 4-6,6-4,3-6 |
| ITF M15 Krsko | 2023/05/19 11:30 | Lucas Gerch v Oliver Ojakaar | 1-6,6-3,6-4 |
| ITF M15 Krsko | 2023/05/19 08:00 | Oliver Ojakaar v Gergely Madarasz | 7-5,6-1 |
| ITF M15 Krsko | 2023/05/18 10:25 | Matic Dimic v Oliver Ojakaar | 3-6,4-6 |
| ITF M15 Doha | 2021/12/15 16:25 | Ryan James Storrie v Oliver Ojakaar | 7-6,6-2 |
| ITF M15 Heraklion | 2023/10/18 06:30 | Andreas Loizas v Szymon Kielan | 1-6,2-6 |
| ITF M15 Danderyd | 2023/09/19 12:25 | Sebastian Eriksson v Szymon Kielan | 6-2,6-3 |
| Challenger Szczecin | 2023/09/10 09:45 | Steven Diez v Szymon Kielan | 6-1,7-5 |
| ITF M15 Koszalin | 2023/09/07 13:25 | Patrick Zahraj v Szymon Kielan | 7-6,6-3 |
| ITF M15 Koszalin | 2023/09/06 12:00 | Alan Bojarski v Szymon Kielan | 7-6,2-6,5-7 |
| ITF M15 Szczawno | 2023/08/30 14:10 | Valerio Perruzza v Szymon Kielan | 6-1,6-1 |
| Challenger Prague | 2023/08/20 09:40 | Michael Vrbensky v Szymon Kielan | 6-2,6-4 |
| Challenger Grodzisk Mazowiecki | 2023/08/13 13:20 | Szymon Kielan v Alex Knaff | 3-6,0-6 |