| ATP - World Tour Finals | 11/20 20:00 | 1 | Daniil Medvedev v Diego Schwartzman | 6-3,6-3 | |
| ATP - World Tour Finals | 11/18 14:25 | 1 | [7] Alexander Zverev v Diego Schwartzman [9] | 6-3,4-6,6-3 | |
| ATP - World Tour Finals | 11/16 14:00 | 1 | [1] Novak Djokovic v Diego Schwartzman [9] | 6-3,6-2 | |
| ATP Paris | 11/06 13:00 | 27 | [9] Diego Schwartzman v Daniil Medvedev [5] | 3-6,1-6 | |
| ATP Paris | 11/05 10:00 | 26 | [9] Diego Schwartzman v Alejandro Davidovich Fokina [63] | 6-1,6-1 | |
| ATP Paris | 11/04 11:20 | 25 | [9] Diego Schwartzman v Richard Gasquet [56] | 7-5,6-3 | |
| ATP Vienna | 10/27 13:00 | 25 | Dusan Lajovic v Diego Schwartzman | Cancelled | |
| ATP - Keulen 2 | 10/25 18:30 | 29 | [7] Alexander Zverev v Diego Schwartzman [9] | 6-2,6-1 | |
| ATP - Keulen 2 | 10/24 19:05 | 28 | [22] Felix Auger Aliassime v Diego Schwartzman [9] | 4-6,7-5,4-6 | |
| ATP - Keulen 2 | 10/23 14:55 | 27 | [64] Alejandro Davidovich Fokina v Diego Schwartzman [9] | 6-2,6-7,1-6 | |
| ATP - Keulen 2 | 10/22 16:00 | 26 | [141] Oscar Otte v Diego Schwartzman [9] | 3-6,2-6 | |
| French Open | 10/09 12:50 | 28 | [14] Diego Schwartzman v Rafael Nadal [2] | 3-6,3-6,6-7 |