Stadium: Center Court Round: 29 Ground: Hardcourt indoor
| 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 |
| Challenger Mouilleron le Captif MD | 2019/10/12 11:00 | O'Mara/Skupski v Jebavy/Zelenay | 6-3,6-3 |
| ATP Sofia MD | 2021/10/02 10:05 | Marach/Oswald v Gonzalez/Molteni | 2-6,7-5,10-6 |
| ATP Sofia MD | 2021/09/30 14:55 | Demoliner/Matos v Marach/Oswald | 6-7,6-7 |
| ATP Sofia MD | 2021/09/28 11:00 | Bopanna/Qureshi v Marach/Oswald | 2-6,7-6,7-10 |
| ATP Metz MD | 2021/09/22 13:20 | Marach/Oswald v Hurkacz/Zielinski | 3-6,4-6 |
| ATP Metz MD | 2021/09/21 13:40 | Marach/Oswald v Mahut/Pospisil | 6-4,6-3 |
| US Open MD | 2021/09/03 15:00 | Marach/Oswald v Erlich/Harris | 2-6,7-6,2-6 |
| ATP Winston-Salem MD | 2021/08/26 19:00 | Arevalo/Middelkoop v Marach/Oswald | 6-3,6-3 |
| ATP Winston-Salem MD | 2021/08/23 20:40 | Marach/Oswald v Gille/Vliegen | 7-6,5-7,10-4 |