| Challenger - Segóvia | 07/26 11:00 | 19 | [348] Ryan Peniston v Luca Vanni [428] | 4-6,3-6 | |
| Challenger - Segóvia | 07/25 14:00 | 14 | [361] Ryan Peniston v Rayane Roumane [404] | 6-1,6-1 | |
| Challenger - Nur-Sultã | 07/23 07:35 | 27 | [361] Ryan Peniston v Pavel Kotov [272] | 4-6,2-6 | |
| Challenger - Nur-Sultã | 07/22 06:25 | 26 | [361] Ryan Peniston v Yu Hsiou Hsu [352] | 6-3,6-4 | |
| Challenger - Nur-Sultã | 07/20 09:10 | 25 | [398] Ergi Kirkin v Ryan Peniston [361] | 2-6,3-6 | |
| Challenger - Nur-Sultã | 07/20 08:00 | 25 | Roman Safiullin v Ryan Peniston | CANC | |
| Challenger - Nur-Sultã | 07/15 07:30 | 26 | [273] Mirza Basic v Ryan Peniston [367] | 6-3,6-1 | |
| Challenger - Nur-Sultã | 07/13 04:00 | 25 | [367] Ryan Peniston v Denis Istomin [196] | 6-1,3-6,6-3 | |
| Wimbledon | 06/22 13:20 | 14 | [116] Yasutaka Uchiyama v Ryan Peniston [375] | 3-6,6-2,6-4 | |
| ATP - Queens | 06/13 12:05 | 19 | [383] Ryan Peniston v Aleksandar Vukic [209] | 6-4,6-7,4-6 | |
| ATP - Queens | 06/12 14:05 | 14 | [158] Marc-Andrea Huesler v Ryan Peniston [383] | 6-4,5-7,4-6 | |
| Challenger - Nottingham | 06/08 11:50 | 25 | [230] Matthew Ebden v Ryan Peniston [383] | 6-4,6-4 |