[1] Novak Djokovic 6-3,6-4 Denis Shapovalov [28] 2019-11-03 14:00
Estadio: Court Central Round: 29 Ground: Hardcourt indoor
Head to Head
| Masters de Shanghái | 2019/10/09 10:30 | Novak Djokovic v Denis Shapovalov | 6-3,6-3 |
| Boodles Challenge | 2019/06/26 13:30 | Novak Djokovic v Denis Shapovalov | 6-7,4-6 |
| ATP Roma | 2019/05/16 11:40 | Novak Djokovic v Denis Shapovalov | 6-1,6-3 |
| Open de Australia | 2019/01/19 04:50 | Novak Djokovic v Denis Shapovalov | 6-3,6-4,4-6,6-0 |
Home History
| ATP París | 2019/11/02 13:00 | Novak Djokovic v Grigor Dimitrov | 7-6,6-4 |
| ATP París | 2019/11/01 14:50 | Novak Djokovic v Stefanos Tsitsipas | 6-1,6-2 |
| ATP París | 2019/10/31 14:15 | Novak Djokovic v Kyle Edmund | 7-6,6-1 |
| ATP París | 2019/10/30 16:20 | Novak Djokovic v Corentin Moutet | 7-6,6-4 |
| Masters de Shanghái | 2019/10/11 06:20 | Novak Djokovic v Stefanos Tsitsipas | 6-3,5-7,3-6 |
| Masters de Shanghái | 2019/10/10 07:00 | Novak Djokovic v John Isner | 7-5,6-3 |
| Masters de Shanghái | 2019/10/09 10:30 | Novak Djokovic v Denis Shapovalov | 6-3,6-3 |
| ATP Tokio | 2019/10/06 06:30 | Novak Djokovic v John Millman | 6-3,6-2 |
Away History
| ATP París | 2019/11/01 18:30 | Denis Shapovalov v Gael Monfils | 6-2,6-2 |
| ATP París | 2019/10/31 16:00 | Alexander Zverev v Denis Shapovalov | 2-6,7-5,2-6 |
| ATP París | 2019/10/30 11:30 | Denis Shapovalov v Fabio Fognini | 3-6,6-3,6-3 |
| ATP Viena | 2019/10/23 10:00 | Pablo Carreno Busta v Denis Shapovalov | 6-3,7-5 |
| ATP Estocolmo | 2019/10/20 13:00 | Denis Shapovalov v Filip Krajinovic | 6-4,6-4 |
| ATP Estocolmo | 2019/10/19 15:30 | Yuichi Sugita v Denis Shapovalov | 5-7,2-6 |
| ATP Estocolmo | 2019/10/18 16:30 | Denis Shapovalov v Cedrik-Marcel Stebe | 6-0,6-3 |
| ATP Estocolmo | 2019/10/17 16:30 | Denis Shapovalov v Alexei Popyrin | 6-4,7-6 |