Stadium: Stadium Round: 24 Ground: Hardcourt outdoor
| Challenger Cary | 2018/09/16 18:50 | James Duckworth v Reilly Opelka | 7-6,6-3 |
| Challenger Charlottesville | 2023/11/01 00:15 | Reilly Opelka v Tennys Sandgren | 6-4,7-5 |
| ATP Washington | 2022/08/04 21:45 | Nick Kyrgios v Reilly Opelka | 7-6,6-2 |
| ATP Washington | 2022/08/03 23:30 | Denis Kudla v Reilly Opelka | 7-6,4-6,4-6 |
| Wimbledon | 2022/06/29 16:30 | Tim Van Rijthoven v Reilly Opelka | 6-4,6-7,7-6,7-6 |
| Wimbledon | 2022/06/27 17:40 | Carlos Taberner v Reilly Opelka | 6-7,4-6,4-6 |
| ATP Eastbourne | 2022/06/20 10:00 | Maxime Cressy v Reilly Opelka | 6-3,6-1 |
| ATP Queens | 2022/06/13 11:00 | Reilly Opelka v Alex De Minaur | 4-6,4-6 |
| French Open | 2022/05/23 09:00 | Filip Krajinovic v Reilly Opelka | 7-6,6-2,6-3 |
| ATP Dallas | 2024/02/07 19:45 | James Duckworth v Christopher Eubanks | 7-6,6-4 |
| ATP Dallas | 2024/02/06 18:00 | James Duckworth v Zachary Svajda | 7-6,6-1 |
| Challenger Cleveland | 2024/02/03 20:40 | James Duckworth v Patrick Kypson | 3-6,6-7 |
| Challenger Cleveland | 2024/02/02 23:40 | James Duckworth v Quinn Vandecasteele | 6-3,7-5 |
| Challenger Cleveland | 2024/01/31 22:00 | James Duckworth v Patrick Maloney | 6-4,6-3 |
| Challenger Cleveland | 2024/01/29 20:20 | James Duckworth v Toby Alex Kodat | 6-3,6-0 |
| Australian Open | 2024/01/15 02:10 | James Duckworth v Luca Van Assche | 7-6,3-6,6-3,3-6,3-6 |
| ATP Brisbane | 2024/01/05 05:00 | Holger Rune v James Duckworth | 6-2,7-6 |