Stadium: Court 2 Round: 27 Ground: Clay
| Challenger Biel MD | 2021/09/21 13:20 | Moraing/Novak v Manafov/Matuszewski | 6-7,3-6 |
| ATP Sofia MD | 2021/10/03 11:00 | O'Mara/Skupski v Marach/Oswald | 6-3,6-4 |
| ATP Sofia MD | 2021/10/02 09:00 | Jebavy/Middelkoop v O'Mara/Skupski | 3-6,1-6 |
| ATP Sofia MD | 2021/10/01 09:00 | Saville/Smith v O'Mara/Skupski | 3-6,6-2,8-10 |
| ATP Sofia MD | 2021/09/30 13:20 | Donski/Kuzmanov v O'Mara/Skupski | 6-2,5-7,7-10 |
| ATP Sofia MD | 2020/11/11 15:35 | Melzer/Roger-Vasselin v O'Mara/Skupski | 6-4,6-2 |
| ATP Sofia MD | 2020/11/09 14:35 | O'Mara/Skupski v Donski/Mladenov | 6-3,6-4 |
| 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 |