Stadium: Stadium 17 Round: 25 Ground: Hardcourt indoor
| ATP Miami | 2019/03/23 20:00 | Reilly Opelka v Diego Schwartzman | 6-4,3-6,6-4 |
| ATP Montreal | 2017/08/07 20:25 | Diego Schwartzman v Reilly Opelka | 6-3,6-7,6-4 |
| UTR Pro Match Series | 2020/05/09 20:20 | Reilly Opelka v Miomir Kecmanovic | 4-3,2-4,4-2 |
| UTR Pro Match Series | 2020/05/09 16:00 | Hubert Hurkacz v Reilly Opelka | 4-2,1-4,4-2 |
| UTR Pro Match Series | 2020/05/08 18:15 | Reilly Opelka v Tommy Paul | 3-4,4-1,4-0 |
| UTR Pro Match Series | 2020/05/08 17:00 | Miomir Kecmanovic v Reilly Opelka | 3-4,0-4 |
| Davis Cup | 2020/03/07 03:00 | Reilly Opelka v Denis Istomin | 6-2,7-5 |
| ATP Delray Beach | 2020/02/23 20:30 | Yoshihito Nishioka v Reilly Opelka | 5-7,7-6,2-6 |
| ATP Delray Beach | 2020/02/23 15:30 | Reilly Opelka v Milos Raonic | 4-6,7-6,6-3 |
| ATP Delray Beach | 2020/02/21 23:00 | Soonwoo Kwon v Reilly Opelka | 3-6,4-6 |
| ATP Buenos Aires | 2020/02/14 22:00 | Diego Schwartzman v Pablo Cuevas | 5-7,7-6,7-5 |
| ATP Buenos Aires | 2020/02/14 02:35 | Diego Schwartzman v Federico Delbonis | 6-3,4-6,6-2 |
| ATP Cordoba | 2020/02/09 22:05 | Diego Schwartzman v Cristian Garin | 6-2,4-6,0-6 |
| ATP Cordoba | 2020/02/09 00:20 | Diego Schwartzman v Laslo Djere | 6-1,1-6,6-2 |
| ATP Cordoba | 2020/02/07 22:50 | Diego Schwartzman v Albert Ramos-Vinolas | 6-0,7-6 |
| ATP Cordoba | 2020/02/07 02:20 | Diego Schwartzman v Jaume Munar | 6-1,7-5 |
| Australian Open | 2020/01/26 03:35 | Diego Schwartzman v Novak Djokovic | 3-6,4-6,4-6 |
| Australian Open | 2020/01/24 00:00 | Diego Schwartzman v Dusan Lajovic | 6-2,6-3,7-6 |