Stadium: Center Court Round: 26 Ground: Hardcourt indoor
| ATP Stockholm MD | 2019/10/16 10:00 | Pavic/Soares v O'Mara/Skupski | 6-4,7-6 |
| Challenger Mouilleron le Captif MD | 2019/10/13 11:00 | Arends/Pel v O'Mara/Skupski | 1-6,4-6 |
| Challenger Mouilleron le Captif MD | 2019/10/12 11:00 | O'Mara/Skupski v Jebavy/Zelenay | 6-3,6-3 |
| Challenger Mouilleron le Captif MD | 2019/10/11 09:00 | Raja/Sancic v O'Mara/Skupski | 3-6,4-6 |
| Challenger Mouilleron le Captif MD | 2019/10/09 17:05 | Halys/Lamasine v O'Mara/Skupski | 0-6,2-6 |
| Challenger Orleans MD | 2019/09/28 12:00 | O'Mara/Skupski v Podlipnik-Castillo/Weissborn | 6-2,6-7,5-10 |
| Challenger Orleans MD | 2019/09/26 14:50 | O'Mara/Skupski v Behar/Ramanathan | 6-3,6-4 |
| Challenger Orleans MD | 2019/09/24 16:50 | O'Mara/Skupski v Donskoy/Ivashka | 6-3,6-4 |