Stadium: C1 Regione Abruzzo Round: 44 Ground: Clay
| ITF M15 - Heraklion | 2021/06/08 08:00 | Petros Tsitsipas v Ioannis Kountourakis | 6-1,7-6 |
| 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 - Gaiba | 2021/06/10 14:45 | Federico Bertuccioli v Tobias Simon | 4-6,3-6 |
| ITF M15 - Gaiba | 2021/06/09 16:15 | Alexander Hoogmartens v Federico Bertuccioli | 7-6,2-6,4-6 |
| ITF M15 - Gaiba | 2021/06/08 08:45 | Lorenzo Bocchi v Federico Bertuccioli | 6-7,0-6 |
| ITF M15 - Gaiba | 2021/06/07 12:30 | Patric Prinoth v Federico Bertuccioli | 4-6,4-6 |
| ITF M15 - Antalya | 2021/05/02 06:00 | Jumpei Yamasaki v Federico Bertuccioli | 6-2,4-6,10-6 |
| ITF M15 - Shymkent | 2021/04/15 03:55 | Federico Bertuccioli v Andrey Chepelev | 5-7,4-6 |
| ITF M15 - Shymkent | 2021/04/14 04:00 | Vladyslav Manafov v Federico Bertuccioli | 4-6,4-6 |
| ITF M15 - Shymkent | 2021/04/13 05:00 | Aleksei Khomich v Federico Bertuccioli | 2-6,4-6 |