Stadium: Court Tsitsipas Round: 25 Ground: Hardcourt outdoor
| ITF - M15 Antalya | 2021/10/29 07:00 | Jack Pinnington Jones v Juan Pablo Paz | 3-6,0-6 |
| ITF - M15 Antalya | 2021/10/28 09:15 | Jack Pinnington Jones v Bulitski, Aliaksandr | 2-6,6-2,7-5 |
| ITF - M15 Antalya | 2021/10/26 08:25 | Peter Heller v Jack Pinnington Jones | 3-6,4-6 |
| ITF - M15 Antalya | 2021/10/21 07:00 | Jack Pinnington Jones v Juan Pablo Paz | 6-7,4-6 |
| ITF - M15 Antalya | 2021/10/19 10:30 | Jack Pinnington Jones v Umut Akkoyun | 6-4,6-3 |
| ITF - M15 Antalya | 2021/10/17 07:00 | Savva Polukhin v Jack Pinnington Jones | 7-6,4-6,2-6 |
| ITF - M15 Antalya | 2021/10/16 06:55 | Jack Pinnington Jones v Manda, Calin | 6-1,6-2 |
| ITF - M15 Antalya | 2021/10/15 07:00 | Jack Pinnington Jones v Mircea-Alexandru Jecan | 6-0,6-1 |
| ITF - M15 Héraklion | 2021/11/16 08:30 | Stamoulos, Ioannis v Veldheer, Mick | 0-6,3-6 |
| ITF - M15 Héraklion | 2021/11/08 09:00 | Stamoulos, Ioannis v Tzicas, Charles | 0-6,3-6 |
| ITF - M15 Héraklion | 2021/11/03 10:15 | Evangelos Kypriotis v Stamoulos, Ioannis | 1-6,6-4,4-6 |
| ITF - M15 Héraklion | 2021/11/02 07:00 | Stamoulos, Ioannis v Christian Fellin | 3-6,6-4,10-8 |
| ITF M15 Sozopol | 2021/09/12 11:00 | Gorbatenko, Vladislav v Stamoulos, Ioannis | 6-2,6-2 |
| ITF M25 Poznan | 2021/08/22 08:00 | Jesse De Jager v Stamoulos, Ioannis | 6-3,6-0 |
| ITF M15 Lodz | 2021/08/15 09:30 | Stamoulos, Ioannis v Alan Bojarski | 3-6,0-6 |
| ITF - M15 Héraklion | 2020/03/02 08:30 | Stamoulos, Ioannis v Pietro Marino | 1-6,2-6 |