Stadium: Court 5 Round: 25 Ground: Hardcourt outdoor
| ITF Greece F10 | 2017/11/22 07:30 | Maksim Tikhomirov v Petros Tsitsipas | 6-3,6-0 |
| ITF M15 Burgas | 2019/10/10 07:00 | Maksim Tikhomirov v Martin Dimitrov | 4-6,3-6 |
| Challenger Columbus 3 | 2019/09/17 20:55 | Gonzalo Escobar v Maksim Tikhomirov | 6-1,4-6,7-5 |
| ITF M15 Szekesfehervar | 2019/09/03 08:00 | Genaro Alberto Olivieri v Maksim Tikhomirov | 6-2,6-4 |
| ITF M25 Gyor | 2019/08/29 08:00 | Maksim Tikhomirov v Lenny Hampel | 1-6,2-6 |
| ITF M25 Gyor | 2019/08/28 08:00 | Maksim Tikhomirov v Mate Voros | 6-3,1-6,6-2 |
| ITF M25 - Pitesti | 2019/08/14 06:00 | Maksim Tikhomirov v Oleg Prihodko | 3-6,2-6 |
| ITF M15 Targu Mures | 2019/08/08 07:00 | Maksim Tikhomirov v Nicholas David Ionel | 4-6,3-6 |
| ITF M15 Targu Mures | 2019/08/07 08:50 | Maksim Tikhomirov v Jake Hersey | 6-3,3-6,7-5 |
| 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 |
| ITF M25 Jounieh | 2019/09/26 13:00 | Petros Tsitsipas v Alexandar Lazarov | 5-7,3-6 |
| ITF M25 Jounieh | 2019/09/24 09:10 | Petros Tsitsipas v Dusan Rajic | 6-4,6-3 |
| ITF M25 Jounieh | 2019/09/23 11:00 | Petros Tsitsipas v Jean-Marie Yazbeck | 6-0,6-0 |