Stadium: Court 8 Round: 26 Ground: Clay
| Challenger Skopje | 2023/05/22 15:10 | Kacper Zuk v Max Houkes | 1-6,1-6 |
| Challenger Tunis | 2023/05/16 08:30 | Sho Shimabukuro v Max Houkes | 6-1,3-6,6-1 |
| Challenger Tunis | 2023/05/14 13:50 | Rayen Hermassi v Max Houkes | 2-6,0-6 |
| Challenger Prague | 2023/05/01 11:05 | Max Houkes v Vitaliy Sachko | 6-4,4-6,5-7 |
| Challenger Prague | 2023/04/30 12:30 | Shintaro Mochizuki v Max Houkes | 6-7,3-6 |
| Challenger Rome | 2023/04/28 09:30 | Sumit Nagal v Max Houkes | 7-5,6-0 |
| Challenger Rome | 2023/04/27 09:00 | Max Houkes v Jelle Sels | 6-4,7-6 |
| Challenger Rome | 2023/04/25 13:15 | Max Houkes v Valentin Vacherot | 4-6,6-3,6-4 |
| Challenger Skopje | 2023/05/23 08:30 | Oliver Crawford v Matheus Pucinelli De Almeida | 6-3,7-6 |
| ITF M25 Kursumlijska Banja | 2023/05/19 10:05 | Marko Topo v Oliver Crawford | 6-3,6-1 |
| ITF M25 Kursumlijska Banja | 2023/05/18 14:00 | Mwendwa Mbithi v Oliver Crawford | 0-6,2-6 |
| ITF M25 Kursumlijska Banja | 2023/05/17 11:15 | Johan A Rodriguez Rodriguez v Oliver Crawford | 3-6,4-6 |
| ITF M25 Varnamo | 2023/05/14 08:15 | Dragos Nicolae Madaras v Oliver Crawford | 7-6,6-1 |
| ITF M25 Varnamo | 2023/05/13 08:15 | Jay Clarke v Oliver Crawford | 7-5,6-7,6-7 |
| ITF M25 Varnamo | 2023/05/12 10:00 | Elmer Moller v Oliver Crawford | 0-6,2-6 |
| ITF M25 Varnamo | 2023/05/11 08:15 | Erik Grevelius v Oliver Crawford | 1-6,2-6 |