Stadium: Stadium Round: 28 Ground: Hardcourt outdoor
| ATP Paris | 2023/11/05 14:00 | Novak Djokovic v Grigor Dimitrov | 6-4,6-3 |
| ATP Rome | 2023/05/14 12:50 | Novak Djokovic v Grigor Dimitrov | 6-3,4-6,6-1 |
| Australian Open | 2023/01/21 08:00 | Grigor Dimitrov v Novak Djokovic | 6-7,3-6,4-6 |
| ATP Paris | 2019/11/02 13:00 | Novak Djokovic v Grigor Dimitrov | 7-6,6-4 |
| ATP Cincinnati | 2018/08/16 22:30 | Novak Djokovic v Grigor Dimitrov | 2-6,6-3,6-4 |
| ATP Queens | 2018/06/21 15:25 | Novak Djokovic v Grigor Dimitrov | 6-4,6-1 |
| ATP Paris | 2016/11/03 14:45 | Novak Djokovic v Grigor Dimitrov | 4-6,6-2,6-3 |
| Wimbledon | 2014/07/04 12:00 | Novak Djokovic v Grigor Dimitrov | 6-4,3-6,7-6,7-6 |
| ATP Indian Wells | 2025/03/08 22:30 | Novak Djokovic v Botic Van De Zandschulp | 2-6,6-3,1-6 |
| ATP Doha | 2025/02/18 16:20 | Novak Djokovic v Matteo Berrettini | 6-7,2-6 |
| Australian Open | 2025/01/21 10:15 | Novak Djokovic v Carlos Alcaraz Garfia | 4-6,6-4,6-3,6-4 |
| Australian Open | 2025/01/19 08:15 | Novak Djokovic v Jiri Lehecka | 6-3,6-4,7-6 |
| Australian Open | 2025/01/17 08:00 | Novak Djokovic v Tomas Machac | 6-1,6-4,6-4 |
| Australian Open | 2025/01/15 03:10 | Novak Djokovic v Jaime Faria | 6-1,6-7,6-3,6-2 |
| Australian Open | 2025/01/13 08:15 | Novak Djokovic v Nishesh Basavareddy | 4-6,6-3,6-4,6-2 |
| ATP Brisbane | 2025/01/03 10:35 | Novak Djokovic v Reilly Opelka | 6-7,3-6 |
| ATP Indian Wells | 2025/03/13 01:00 | Grigor Dimitrov v Carlos Alcaraz Garfia | 1-6,1-6 |
| ATP Indian Wells | 2025/03/11 03:30 | Grigor Dimitrov v Gael Monfils | 7-6,4-6,7-6 |
| ATP Indian Wells | 2025/03/09 01:40 | Grigor Dimitrov v Nuno Borges | 6-3,6-4 |
| ATP Doha | 2025/02/17 13:45 | Jiri Lehecka v Grigor Dimitrov | 6-4,6-4 |
| ATP Brisbane | 2025/01/01 03:20 | Aleksandar Vukic v Grigor Dimitrov | 2-6,6-7 |
| ATP Brisbane | 2024/12/30 06:00 | Yannick Hanfmann v Grigor Dimitrov | 6-7,3-6 |
| ATP Paris | 2024/11/01 20:10 | Grigor Dimitrov v Karen Khachanov | 2-6,3-6 |
| ATP Paris | 2024/10/31 20:50 | Grigor Dimitrov v Arthur Rinderknech | 6-2,4-6,7-6 |