| Date | R | Kodus v Võõrsil | - |
|---|---|---|---|
| 10/23 13:30 | 29 | [5] Stefanos Tsitsipas v Holger N Rune [27] | 4-6,4-6 |
| 10/22 16:00 | 28 | [5] Stefanos Tsitsipas v Emil Ruusuvuori [52] | 6-2,6-2 |
| 10/21 16:00 | 27 | [5] Stefanos Tsitsipas v Mikael Ymer [79] | 7-5,6-3 |
| 10/19 19:10 | 26 | [5] Stefanos Tsitsipas v Maxime Cressy [33] | 7-6,7-6 |
| 10/21 13:05 | 29 | [145] Ernests Gulbis v Stefanos Tsitsipas [16] | 4-6,4-6 |
| 10/20 11:00 | 28 | [16] Stefanos Tsitsipas v Fabio Fognini [14] | 6-3,6-2 |
| 10/19 14:00 | 27 | [35] Philipp Kohlschreiber v Stefanos Tsitsipas [16] | 3-6,6-7 |
| 10/17 14:10 | 26 | [33] John Millman v Stefanos Tsitsipas [16] | 4-6,6-3,3-6 |