| ATP Antwerp | 10/21 12:00 | 25 | [28] Taylor Fritz v Reilly Opelka [33] | 7-6,6-1 | |
| ATP St Petersburg | 10/16 13:20 | 27 | [36] Reilly Opelka v Borna Coric [27] | 6-7,3-6 | |
| ATP St Petersburg | 10/15 14:00 | 26 | [6] Daniil Medvedev v Reilly Opelka [36] | 6-2,5-7,4-6 | |
| ATP St Petersburg | 10/14 10:00 | 25 | [308] Nino Serdarusic v Reilly Opelka [36] | 6-3,6-7,2-6 | |
| ATP St Petersburg | 10/13 10:00 | 25 | Jannik Sinner v Reilly Opelka | Cancelled | |
| French Open | 09/28 10:55 | 23 | [36] Reilly Opelka v Jack Sock [310] | 4-6,4-6,3-6 | |
| US Open | 08/31 22:35 | 23 | [35] Reilly Opelka v David Goffin [10] | 6-7,6-3,1-6,4-6 | |
| ATP New York | 08/26 21:15 | 27 | [39] Reilly Opelka v Stefanos Tsitsipas [6] | Retired | |
| ATP New York | 08/25 19:55 | 26 | [8] Matteo Berrettini v Reilly Opelka [39] | 3-6,6-7 | |
| ATP New York | 08/24 17:50 | 25 | [39] Reilly Opelka v Diego Schwartzman [13] | 6-3,7-6 | |
| ATP New York | 08/22 16:35 | 24 | [77] Cameron Norrie v Reilly Opelka [39] | 3-6,4-6 | |
| All American Team Cup | 07/05 16:00 | - | Sam Querrey v Reilly Opelka | Cancelled |