[29] Grigor Dimitrov 4-6,6-4,4-6 Casper Ruud [10] 2021-10-02 23:15
Stadium: Barnes Stadium Round: 28 Ground: Hardcourt outdoor
Home History
| ATP - San Diego | 2021/10/02 02:10 | Aslan Karatsev v Grigor Dimitrov | 1-6,6-1,2-6 |
| ATP - San Diego | 2021/10/01 02:35 | Grigor Dimitrov v August Holmgren | 6-1,6-1 |
| ATP - San Diego | 2021/09/28 21:00 | Marton Fucsovics v Grigor Dimitrov | 3-6,6-1,5-7 |
| US Open | 2021/08/30 19:10 | Grigor Dimitrov v Sam Riffice | 6-1,7-6,6-3 |
| ATP - Cincinnati | 2021/08/19 16:05 | Daniil Medvedev v Grigor Dimitrov | 6-3,6-3 |
| ATP - Cincinnati | 2021/08/18 14:00 | Alexander Bublik v Grigor Dimitrov | 3-6,5-7 |
| ATP - Cincinnati | 2021/08/17 15:00 | Grigor Dimitrov v Roberto Bautista-Agut | 6-3,6-4 |
| ATP - Toronto | 2021/08/11 02:35 | Grigor Dimitrov v Reilly Opelka | 3-6,4-6 |
Away History
| ATP - San Diego | 2021/10/02 00:30 | Lorenzo Sonego v Casper Ruud | 1-6,4-6 |
| ATP - San Diego | 2021/10/01 00:30 | Andy Murray v Casper Ruud | 5-7,4-6 |
| Laver Cup | 2021/09/24 17:00 | Casper Ruud v Reilly Opelka | 6-3,7-6 |
| Davis Cup | 2021/09/18 13:45 | Casper Ruud v Sanjar Fayziev | 6-3,6-1 |
| Davis Cup | 2021/09/17 15:50 | Casper Ruud v Khumoyun Sultanov | 6-3,6-3 |
| US Open | 2021/09/01 16:00 | Casper Ruud v Botic Van De Zandschulp | 6-3,4-6,3-6,4-6 |
| US Open | 2021/08/30 18:45 | Casper Ruud v Yuichi Sugita | 6-3,6-2,6-2 |
| ATP - Cincinnati | 2021/08/21 00:30 | Casper Ruud v Alexander Zverev | 1-6,3-6 |