Stadium: Hard Court Central Round: 25 Ground: Hardcourt outdoor
| ITF M15 Heraklion | 2021/06/03 09:00 | Billy Harris v Petros Tsitsipas | 4-6,6-0,7-6 |
| ITF M15 Heraklion | 2021/06/02 08:20 | Petros Tsitsipas v Alec Deckers | 6-4,6-4 |
| ITF M15 Heraklion | 2021/05/27 10:45 | Petros Tsitsipas v Daniel Cox | 6-4,0-6,1-6 |
| ATP Marseille | 2021/03/09 17:55 | Alejandro Davidovich Fokina v Petros Tsitsipas | 6-0,6-2 |
| ITF M15 Monastir | 2020/12/24 10:20 | Kaichi Uchida v Petros Tsitsipas | 6-3,6-2 |
| ITF M15 Monastir | 2020/12/22 08:30 | Petros Tsitsipas v Oscar Moraing | 1-6,6-4,7-6 |
| ITF M15 Monastir | 2020/12/17 12:55 | Petros Tsitsipas v Luca Giacomini | 6-2,4-6,2-6 |
| ITF M15 Monastir | 2020/12/15 08:00 | Simone Roncalli v Petros Tsitsipas | 4-6,3-6 |
| ITF M15 Heraklion | 2021/05/30 11:00 | Eduardo Cohen v Ioannis Kountourakis | 4-6,6-0,10-7 |
| ITF M15 Heraklion | 2021/05/23 06:30 | Ioannis Kountourakis v Christos Avraam | 6-1,4-6,7-10 |
| ITF M15 Heraklion | 2021/05/16 10:30 | Ioannis Kountourakis v David Eisenzapf | 3-6,1-6 |
| ITF M15 Monastir | 2021/04/05 08:00 | Ioannis Kountourakis v Vitali Shvets | 4-6,6-0,6-10 |
| ITF M15 Monastir | 2021/04/04 09:00 | Simon Yitbarek v Ioannis Kountourakis | 4-6,6-2,7-10 |
| ITF M15 Monastir | 2021/03/28 11:30 | Ioannis Kountourakis v Tomas Liska | 3-6,4-6 |
| ITF M15 Manacor | 2021/01/10 11:00 | Ioannis Kountourakis v Peter Goldsteiner | 4-6,4-6 |
| ITF M15 Manacor | 2021/01/04 10:00 | Ioannis Kountourakis v Joan B B Isern | 5-7,0-6 |