Stadium: Court 14 Round: 27 Ground: Hardcourt outdoor
| ITF - M15 Heraklion | 2023/10/19 09:25 | Oleg Prihodko v Alessandro Pecci | 6-4,6-3 |
| ITF - M15 Heraklion | 2023/10/18 06:30 | Oleg Prihodko v Thomas Braithwaite | 6-3,6-4 |
| UTR Pro Beograd | 2023/10/08 09:35 | Ilya Snitari v Oleg Prihodko | 6-7,6-7 |
| UTR Pro Beograd | 2023/10/07 11:06 | Sasa Markovic v Oleg Prihodko | 2-6,6-7 |
| UTR Pro Beograd | 2023/10/06 06:00 | Vuk Radjenovic v Oleg Prihodko | 2-6,2-6 |
| UTR Pro Beograd | 2023/10/03 14:22 | Ivan Sodan v Oleg Prihodko | 0-6,1-6 |
| UTR Pro Beograd | 2023/10/02 12:13 | Gabriel Matuszewski v Oleg Prihodko | 2-6,4-6 |
| UTR Pro Beograd | 2023/10/01 11:04 | Oleg Prihodko v Illya Beloborodko | 6-1,6-4 |
| ITF - M15 Heraklion | 2023/10/19 06:30 | Oliver Ojakaar v Szymon Kielan | 7-6,7-6 |
| 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 |