| ITF - M15 Heraklion | 11/28 08:00 | 28 | Adrian Andreev v Ryan Peniston | 6-4,6-4 | |
| ITF - M15 Heraklion | 11/27 10:10 | 27 | [379] Ryan Peniston v Gijs Brouwer [466] | 5-7,6-2,6-1 | |
| ITF - M15 Heraklion | 11/26 09:05 | 26 | Ryan Peniston v Sebastian Gima | 6-4,6-1 | |
| ITF - M15 Heraklion | 11/25 12:45 | 25 | Ryan Peniston v Matic Spec | 6-4,6-1 | |
| ITF - M15 Heraklion | 11/18 09:15 | 25 | Ryan Peniston v Stuart Parker | 6-1,3-6,2-6 | |
| ITF - M15 Heraklion | 11/14 09:25 | 28 | Evan Furness v Ryan Peniston | 6-2,6-2 | |
| ITF - M15 Heraklion | 11/13 11:30 | 27 | Ryan Peniston v Corentin Denolly | Retired | |
| ITF - M15 Heraklion | 11/13 07:30 | 26 | Ryan Peniston v Artem Dubrivnyy | 6-2,6-1 | |
| ITF - M15 Heraklion | 11/12 11:00 | 25 | Ryan Peniston v Sahar Simon | 6-0,6-2 | |
| ITF - M15 Heraklion | 11/07 09:00 | 28 | [448] Lucas Catarina v Ryan Peniston [396] | 6-4,4-6,7-5 | |
| ITF - M15 Heraklion | 11/07 08:00 | 27 | Ryan Peniston v Matija Pecotic | Walkover | |
| ITF - M15 Heraklion | 11/06 08:00 | - | Ryan Peniston v Matija Pecotic | View |