Stadium: Hard 17 Round: 27 Ground: Hardcourt outdoor
| ITF M25 Heraklion | 2023/11/02 10:00 | Guy Den Ouden v Kielan, Szymon | 7-5,6-0 |
| ITF M25 Heraklion | 2023/11/01 11:55 | Guy Den Ouden v 피에트리, 벤자민 | 2-6,6-3,6-2 |
| ITF M15 Heraklion | 2023/10/27 07:00 | Guy Den Ouden v 헤이노넨, 아담 | 6-7,6-1,2-6 |
| ITF M15 Heraklion | 2023/10/25 06:30 | Guy Den Ouden v Ioannis Kountourakis | 7-5,6-4 |
| ITF M15 Heraklion | 2023/10/20 07:00 | Guy Den Ouden v Jakub Nicod | 2-6,6-7 |
| ITF M15 Heraklion | 2023/10/19 08:45 | 돈데르스, 닥스 v Guy Den Ouden | 6-7,5-7 |
| ITF M15 Heraklion | 2023/10/18 07:25 | Guy Den Ouden v Matthew William Donald | 6-4,6-2 |
| ITF M15 Heraklion | 2023/10/17 06:30 | Guy Den Ouden v 쿠아일, 다비드 | 6-1,7-5 |
| ITF M25 Heraklion | 2023/11/02 08:00 | 올로브, 블라디슬라브 v 포르티, 프란세스코 | 6-1,6-1 |
| ITF M25 Heraklion | 2023/11/01 08:35 | 올로브, 블라디슬라브 v 돈데르스, 닥스 | 6-1,6-4 |
| ITF M15 Heraklion | 2023/10/26 06:30 | 트린커, 조나스 v 올로브, 블라디슬라브 | 6-4,1-6,6-2 |
| Challenger Olbia | 2023/10/18 09:45 | 올로브, 블라디슬라브 v 자쿠에트, 키리안 | 7-5,3-6,4-6 |
| Challenger Olbia | 2023/10/16 08:00 | Kasnikowski, Maks v 올로브, 블라디슬라브 | 6-4,6-7,4-6 |
| Challenger Olbia | 2023/10/15 08:00 | 카데, 알준 v 올로브, 블라디슬라브 | 0-6,3-6 |
| Alicante, Spain | 2023/10/01 13:05 | Pokorny, Lukas v 올로브, 블라디슬라브 | 6-3,6-0 |
| ITF M25 Zlatibor | 2023/09/29 13:30 | Topo, Marko v 올로브, 블라디슬라브 | 6-1,6-2 |