Stadium: Court 3 Round: 44 Ground: Clay
| ITF M15 Kursumlijska Banja | 2023/05/28 14:00 | Bautista Vilicich v Milan Drinic | 5-7,6-4,8-10 |
| ITF M15 Brcko | 2023/05/23 07:30 | Igor Gimenez v Milan Drinic | 7-6,6-4 |
| ITF M15 Brcko | 2023/05/22 13:00 | Vitali Shvets v Milan Drinic | 1-6,3-6 |
| ITF M25 Kursumlijska Banja | 2023/05/19 10:10 | Milan Drinic v Mikalai Haliak | 3-6,3-6 |
| ITF M25 Kursumlijska Banja | 2023/05/18 15:30 | Miljan Zekic v Milan Drinic | 3-6,6-3,6-7 |
| ITF M25 Kursumlijska Banja | 2023/05/17 07:00 | Milan Drinic v Timofey Stepanov | 3-6,6-3,7-5 |
| ITF M25 Kursumlijska Banja | 2023/05/16 06:55 | Milan Drinic v Nikola Mitrovic | 6-1,6-2 |
| ITF M25 Kursumlijska Banja | 2023/05/15 07:00 | Milan Drinic v Pavle Daljev | 7-5,6-4 |
| ITF M15 Kursumlijska Banja | 2023/05/29 15:10 | Nikola Jovanovic v Nicolas Villalon | 2-6,2-6 |
| ITF M15 Addis Ababa | 2023/05/25 06:00 | Nicolas Villalon v Digvijay Pratap Singh | 2-6,1-6 |
| ITF M15 Addis Ababa | 2023/05/23 12:00 | Nicolas Villalon v Ryotaro Matsumura | 6-4,6-2 |
| ITF M15 Addis Ababa Qual | 2023/05/22 06:50 | Nicolas Villalon v Linus Videhult | 6-3,6-7,10-5 |
| ITF M15 Addis Ababa Qual | 2023/05/21 05:30 | Nicolas Villalon v Ayush Sharma | 6-4,6-3 |
| ITF M15 Addis Ababa | 2023/05/18 09:55 | Nicolas Villalon v Eric Vanshelboim | 1-6,4-6 |
| ITF M15 Addis Ababa | 2023/05/18 05:30 | Nitin Kumar Sinha v Nicolas Villalon | 6-3,3-6,6-7 |
| ITF M15 Addis Ababa | 2023/05/15 09:15 | Nicolas Villalon v Raffael Schaer | 3-6,6-3,10-7 |