Stadium: Center Court Round: 28 Ground: Hardcourt indoor
| ATP Sofia MD | 2021/09/30 17:00 | Erlich/Inglot v Jebavy R / Middelkoop M | 2-6,5-7 |
| ATP Sofia MD | 2021/09/28 13:55 | Jebavy R / Middelkoop M v Andreev A / Lazarov A | 6-2,6-4 |
| ATP Kitzbuhel MD | 2021/07/31 11:00 | Erler/Miedler v Jebavy R / Middelkoop M | 7-5,7-6 |
| ATP Kitzbuhel MD | 2021/07/30 16:15 | Jebavy R / Middelkoop M v Martinez/Polmans | 6-3,1-6,10-7 |
| ATP Kitzbuhel MD | 2021/07/28 11:20 | Begemann/Zelenay v Jebavy R / Middelkoop M | 7-6,3-6,9-11 |
| ATP Kitzbuhel MD | 2021/07/27 11:20 | Martinez/Sitak v Jebavy R / Middelkoop M | 7-6,4-6,1-10 |
| US Open MD | 2019/08/29 22:45 | Jebavy R / Middelkoop M v Haase R / Koolhof W | 4-6,4-6 |
| Challenger Meerbusch MD | 2019/08/16 11:00 | Jebavy R / Middelkoop M v Balaji N S / Vardhan V | 6-7,3-6 |
| ATP Sofia MD | 2021/10/01 09:00 | Saville L / Smith J-P 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 J / Roger-Vasselin E 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 M / Soares B v O'Mara / Skupski | 6-4,7-6 |
| Challenger Mouilleron le Captif MD | 2019/10/13 11:00 | Arends S / Pel D v O'Mara / Skupski | 1-6,4-6 |
| Challenger Mouilleron le Captif MD | 2019/10/12 11:00 | O'Mara / Skupski v Jebavy R / Zelenay I | 6-3,6-3 |
| Challenger Mouilleron le Captif MD | 2019/10/11 09:00 | Raja P / Sancic A v O'Mara / Skupski | 3-6,4-6 |