[1] Novak Djokovic 6-3,6-3 Denis Shapovalov [36] 2019-10-09 10:30
Stadium: Center Court 1 Round: 25 Ground: Hardcourt outdoor
Head to Head
| Boodles Challenge | 2019/06/26 13:30 | Novak Djokovic v Denis Shapovalov | 6-7,4-6 |
| ATP Rome | 2019/05/16 11:40 | Novak Djokovic v Denis Shapovalov | 6-1,6-3 |
| Australian Open | 2019/01/19 04:50 | Novak Djokovic v Denis Shapovalov | 6-3,6-4,4-6,6-0 |
Home History
| ATP Tokyo | 2019/10/06 06:30 | Novak Djokovic v John Millman | 6-3,6-2 |
| ATP Tokyo | 2019/10/05 06:00 | Novak Djokovic v David Goffin | 6-3,6-4 |
| ATP Tokyo | 2019/10/04 05:15 | Novak Djokovic v Lucas Pouille | 6-1,6-2 |
| ATP Tokyo | 2019/10/02 07:20 | Novak Djokovic v Go Soeda | 6-3,7-5 |
| ATP Tokyo | 2019/10/01 06:10 | Novak Djokovic v Alexei Popyrin | 6-4,6-2 |
| US Open | 2019/08/31 00:45 | Novak Djokovic v Denis Kudla | 6-3,6-4,6-2 |
| US Open | 2019/08/28 23:00 | Novak Djokovic v Juan Ignacio Londero | 6-4,7-6,6-1 |
| US Open | 2019/08/26 18:05 | Novak Djokovic v Roberto Carballes Baena | 6-4,6-1,6-4 |
Away History
| ATP Shanghai | 2019/10/07 04:30 | Frances Tiafoe v Denis Shapovalov | 4-6,2-6 |
| ATP Tokyo | 2019/10/03 05:25 | David Goffin v Denis Shapovalov | 7-6,7-6 |
| ATP Tokyo | 2019/10/01 08:00 | Denis Shapovalov v Miomir Kecmanovic | 6-4,6-4 |
| ATP Chengdu | 2019/09/28 07:15 | Denis Shapovalov v Pablo Carreno Busta | 3-6,4-6 |
| ATP Chengdu | 2019/09/27 10:10 | Egor Gerasimov v Denis Shapovalov | 4-6,6-3,3-6 |
| ATP Chengdu | 2019/09/26 06:35 | Bradley Klahn v Denis Shapovalov | 6-3,3-6,6-7 |
| ATP Chengdu | 2019/09/25 09:20 | Ricardas Berankis v Denis Shapovalov | 4-6,3-6 |
| Laver Cup | 2019/09/20 11:00 | Dominic Thiem v Denis Shapovalov | 6-4,5-7,13-11 |