Stadium: Court Tsitsipas Round: 25 Ground: Hardcourt outdoor
| ITF - M15 Heraklion | 2021/11/02 07:00 | Evangelos Kypriotis v Alan Gleeson | 2-6,7-6,10-7 |
| ITF - M15 Heraklion | 2021/11/01 08:00 | Igor Shrolik v Evangelos Kypriotis | 0-6,1-6 |
| ITF - M15 Heraklion | 2021/05/30 09:00 | Evangelos Kypriotis v Adam Jones | 6-1,3-6,10-7 |
| ITF - M15 Heraklion | 2021/05/18 08:00 | Evangelos Kypriotis v Matthew Dellavedova | 1-6,3-6 |
| ITF - M15 Heraklion | 2021/05/17 07:00 | Petr Hajek v Evangelos Kypriotis | 6-4,0-6,8-10 |
| ITF - M15 Heraklion | 2021/11/02 07:00 | Ioannis Stamoulos v Christian Fellin | 3-6,6-4,10-8 |
| ITF M15 - Sozopol | 2021/09/12 11:00 | Vladislav Gorbatenko v Ioannis Stamoulos | 6-2,6-2 |
| ITF - M25 Poznan | 2021/08/22 08:00 | Jesse De Jager v Ioannis Stamoulos | 6-3,6-0 |
| ITF M15 - Łódź | 2021/08/15 09:30 | Ioannis Stamoulos v Alan Bojarski | 3-6,0-6 |
| ITF - M15 Heraklion | 2020/03/02 08:30 | Ioannis Stamoulos v Pietro Marino | 1-6,2-6 |
| ITF - M15 Heraklion | 2020/02/26 13:20 | Coleman Wong v Ioannis Stamoulos | 6-3,5-7,6-0 |
| ITF - M15 Heraklion | 2020/02/16 08:30 | Edward Hubner v Ioannis Stamoulos | 6-3,6-1 |
| ITF - M15 Heraklion | 2020/02/11 09:30 | Ioannis Stamoulos v Stefan Seifert | 0-6,6-2,3-6 |