| ITF - M25 - Quinta Do Lago | 10/18 13:35 | 62 | Ryan Peniston v Gian Luca Tanner | Retired | |
| ITF - M25 - Quinta Do Lago | 10/17 12:00 | 62 | Ryan Peniston v Andre Meinertz | 6-0,6-0 | |
| Challenger - Columbus | 09/22 15:45 | 26 | [309] Ryan Peniston v Max Purcell [189] | 3-6,6-7 | |
| Challenger - Columbus | 09/20 16:40 | 25 | [166] Jason Jung v Ryan Peniston [309] | 3-6,4-6 | |
| Challenger - Cary | 09/18 00:40 | 27 | [323] Ryan Peniston v Bjorn Fratangelo [189] | 3-6,5-7 | |
| Challenger - Cary | 09/16 22:55 | 26 | [199] Christopher Eubanks v Ryan Peniston [323] | 6-4,6-7,4-6 | |
| Challenger - Cary | 09/14 15:00 | 25 | [323] Ryan Peniston v Peter Polansky [232] | 6-3,6-2 | |
| ITF - M25 - Ricany | 09/04 08:25 | 28 | [331] Ryan Peniston v Yshai Oliel [390] | Retired | |
| ITF - M25 - Ricany | 09/03 10:15 | 27 | [419] Mateus Alves v Ryan Peniston [331] | 4-6,2-6 | |
| ITF - M25 - Ricany | 09/02 08:00 | 26 | Alexander Donski v Ryan Peniston | 2-6,4-6 | |
| ITF - M25 - Ricany | 08/31 09:20 | 25 | Jiri Jenicek v Ryan Peniston | 2-6,0-6 | |
| Challenger - Prag | 08/28 09:00 | 29 | [351] Ryan Peniston v Franco Agamenone [330] | 3-6,1-6 |