| Wimbledon | 06/29 11:30 | 24 | [135] Ryan Peniston v Steve Johnson [93] | 3-6,2-6,4-6 | |
| Wimbledon | 06/28 10:00 | 23 | [135] Ryan Peniston v Henri Laaksonen [96] | 6-4,6-3,6-2 | |
| ATP Eastbourne | 06/23 12:55 | 27 | [108] Jack Draper v Ryan Peniston [147] | 6-3,6-3 | |
| ATP Eastbourne | 06/23 11:00 | 26 | [49] Pedro Martinez v Ryan Peniston [147] | 6-7,6-3,3-6 | |
| ATP Eastbourne | 06/21 10:00 | 25 | [147] Ryan Peniston v Holger Vitus Nodskov Rune [29] | 4-6,7-6,6-1 | |
| ATP Queens | 06/17 14:05 | 27 | [180] Ryan Peniston v Filip Krajinovic [48] | 6-4,3-6,3-6 | |
| ATP Queens | 06/16 15:25 | 26 | [180] Ryan Peniston v Francisco Cerundolo [46] | 6-0,4-6,6-4 | |
| ATP Queens | 06/14 12:15 | 25 | [5] Casper Ruud v Ryan Peniston [180] | 6-7,6-7 | |
| Challenger Nottingham | 06/10 10:00 | 27 | [100] Alexei Popyrin v Ryan Peniston [197] | 6-3,6-4 | |
| Challenger Nottingham | 06/08 11:00 | 26 | [192] Borna Gojo v Ryan Peniston [197] | 4-6,6-7 | |
| Challenger Nottingham | 06/07 14:15 | 25 | [197] Ryan Peniston v Jiri Vesely [76] | 6-7,7-6,7-6 | |
| Challenger Surbiton | 06/03 15:50 | 27 | [375] Otto Virtanen v Ryan Peniston [195] | 6-7,6-3,7-6 |