Round: 26 Ground: Clay
| Challenger Drummondville | 2016/03/17 20:20 | Denis Shapovalov v Austin Krajicek | 6-3,7-5 |
| Challenger Drummondville | 2016/03/16 17:20 | Denis Shapovalov v Filip Peliwo | 6-2,3-6,6-1 |
| ITF Canada F1 | 2016/03/03 18:10 | Denis Shapovalov v Liam Broady | 4-6,0-6 |
| ITF Canada F1 | 2016/03/02 19:00 | Denis Shapovalov v Iancu-Iustinian Ghinda | 6-1,6-1 |
| ITF USA F5 | 2016/01/31 17:45 | Pedro Sakamoto v Denis Shapovalov | 6-7,3-6 |
| ITF USA F5 | 2016/01/30 19:00 | Denis Shapovalov v Jaume Pla Malfeito | 6-0,6-1 |
| ITF USA F5 | 2016/01/30 15:30 | Mateo Nicolas Martinez v Denis Shapovalov | 1-6,2-6 |
| ITF USA F5 | 2016/01/29 19:00 | Denis Shapovalov v Jason Kubler | 6-1,6-3 |