Round: 44 Ground: Hardcourt outdoor
| ITF M25 Monastir | 2019/10/23 09:00 | Skander Mansouri v Alafia Ayeni | 6-3,6-3 |
| ITF M25 Rodez | 2019/10/14 09:25 | Alafia Ayeni v Nikolay Vylegzhanin | 4-6,1-6 |
| Challenger Nur-Sultan 2 | 2019/09/30 04:00 | Savriyan Danilov v Alafia Ayeni | 4-6,7-6,6-4 |
| ITF M25 Almaty | 2019/09/27 05:00 | Alafia Ayeni v Jurij Rodionov | 4-6,4-6 |
| ITF M25 Almaty | 2019/09/24 06:55 | Alafia Ayeni v Cing-Yang Meng | 6-2,7-5 |
| Challenger Shanghai | 2019/09/09 08:10 | Mukund Sasikumar v Alafia Ayeni | 6-4,6-1 |
| Challenger New Haven | 2019/09/03 14:00 | Ulises Blanch v Alafia Ayeni | 6-3,6-2 |
| Challenger Yokkaichi | 2019/08/06 07:20 | Yunseong Chung v Alafia Ayeni | 7-6,6-3 |
| ITF M25 Monastir | 2019/10/27 14:00 | Petros Tsitsipas v Adam Nagoudi | 6-4,6-4 |
| ITF M25 Monastir | 2019/10/27 10:30 | Buvaysar Gadamauri v Petros Tsitsipas | 3-6,4-6 |
| ITF M25 Monastir | 2019/10/22 09:00 | Maksim Tikhomirov v Petros Tsitsipas | 6-2,1-6,6-1 |
| ITF M25 Monastir | 2019/10/21 09:00 | Petros Tsitsipas v Buvaysar Gadamauri | 6-4,6-3 |
| ITF M15 Antalya | 2019/10/08 07:00 | Petros Tsitsipas v Philip Bachmaier | 7-6,6-7,8-10 |
| ITF M15 Antalya | 2019/10/07 07:00 | Petros Tsitsipas v Bekir Berk Sahin | 7-6,6-0 |
| ITF M25 Jounieh | 2019/10/02 18:15 | Mate Valkusz v Petros Tsitsipas | 6-3,7-5 |
| ITF M25 Jounieh | 2019/09/30 11:15 | Eric Ahren Moonga v Petros Tsitsipas | 4-6,2-6 |