| ATP - World Tour Finals | 11/19 20:25 | 1 | [2] Rafael Nadal v Stefanos Tsitsipas [6] | 6-4,4-6,6-2 | |
| ATP - World Tour Finals | 11/17 20:00 | 2 | [6] Stefanos Tsitsipas v Andrey Rublev [8] | 6-1,4-6,7-6 | |
| ATP - World Tour Finals | 11/15 14:25 | 1 | [3] Dominic Thiem v Stefanos Tsitsipas [6] | 7-6,4-6,6-3 | |
| ATP Paris | 11/03 18:10 | 25 | [34] Ugo Humbert v Stefanos Tsitsipas [6] | 7-6,6-7,7-6 | |
| ATP Vienna | 10/29 18:50 | 26 | [5] Stefanos Tsitsipas v Grigor Dimitrov [20] | 7-6,4-6,3-6 | |
| ATP Vienna | 10/28 14:25 | 25 | [5] Stefanos Tsitsipas v Jan-Lennard Struff [34] | 6-7,6-3,6-4 | |
| French Open | 10/09 16:20 | 28 | [1] Novak Djokovic v Stefanos Tsitsipas [6] | 6-3,6-2,5-7,4-6,6-1 | |
| French Open | 10/07 14:05 | 27 | [12] Andrey Rublev v Stefanos Tsitsipas [6] | 5-7,2-6,3-6 | |
| French Open | 10/05 10:45 | 26 | [20] Grigor Dimitrov v Stefanos Tsitsipas [6] | 3-6,6-7,2-6 | |
| French Open | 10/03 12:40 | 25 | [56] Aljaz Bedene v Stefanos Tsitsipas [6] | Retired | |
| French Open | 10/01 14:25 | 24 | [60] Pablo Cuevas v Stefanos Tsitsipas [6] | 1-6,4-6,2-6 | |
| French Open | 09/29 15:20 | 23 | [109] Jaume Munar v Stefanos Tsitsipas [6] | 6-4,6-2,1-6,4-6,4-6 |