| ATP - Sófia | 11/10 16:00 | 26 | [12] Denis Shapovalov v Radu Albot [93] | 2-6,4-6 | |
| ATP - Viena | 10/26 18:40 | 25 | [153] Jurij Rodionov v Denis Shapovalov [12] | 6-4,7-5 | |
| ATP - Colónia 2 | 10/22 13:35 | 26 | [12] Denis Shapovalov v Gilles Simon [58] | 1-6,6-4,2-6 | |
| ATP - São Peterburgo | 10/17 11:00 | 28 | [10] Andrey Rublev v Denis Shapovalov [12] | 4-6,6-3,6-4 | |
| ATP - São Peterburgo | 10/16 11:20 | 27 | [18] Stan Wawrinka v Denis Shapovalov [12] | 4-6,5-7 | |
| ATP - São Peterburgo | 10/15 10:00 | 26 | [141] Ilya Ivashka v Denis Shapovalov [12] | 1-6,4-6 | |
| ATP - São Peterburgo | 10/14 10:00 | 25 | [197] Viktor Troicki v Denis Shapovalov [12] | 2-6,3-6 | |
| ATP - São Peterburgo | 10/13 10:00 | 25 | Sam Querrey v Denis Shapovalov | Cancelled | |
| ATP - São Peterburgo | 10/13 08:00 | - | Sam Querrey v Denis Shapovalov | View | |
| Open de França | 10/01 09:00 | 24 | [11] Denis Shapovalov v Roberto Carballes Baena [101] | 5-7,7-6,3-6,6-3,6-8 | |
| Open de França | 09/29 16:00 | 23 | [11] Denis Shapovalov v Gilles Simon [54] | 6-2,7-5,5-7,6-3 | |
| ATP - Roma | 09/20 17:00 | 28 | [14] Denis Shapovalov v Diego Schwartzman [15] | 4-6,7-5,6-7 |