[3] Roger Federer 6-3,4-6,6-3,4-6,2-6 Grigor Dimitrov [78] 2019-09-04 00:15
Stadium: Arthur Ashe Stadium Round: 27 Ground: Hardcourt outdoor
Head to Head
| ATP Rotterdam | 2018/02/18 14:30 | Roger Federer v Grigor Dimitrov | 6-2,6-2 |
| Wimbledon | 2017/07/10 16:00 | Grigor Dimitrov v Roger Federer | 4-6,2-6,4-6 |
Home History
| US Open | 2019/09/01 16:00 | Roger Federer v David Goffin | 6-2,6-2,6-0 |
| US Open | 2019/08/30 16:00 | Roger Federer v Daniel Evans | 6-2,6-2,6-1 |
| US Open | 2019/08/28 17:25 | Roger Federer v Damir Dzumhur | 3-6,6-2,6-3,6-4 |
| US Open | 2019/08/27 01:00 | Roger Federer v Sumit Nagal | 4-6,6-1,6-2,6-4 |
| ATP Cincinnati | 2019/08/15 19:30 | Roger Federer v Andrey Rublev | 3-6,4-6 |
| ATP Cincinnati | 2019/08/13 23:00 | Roger Federer v Juan Ignacio Londero | 6-3,6-4 |
| Wimbledon | 2019/07/14 13:00 | Novak Djokovic v Roger Federer | 7-6,1-6,7-6,4-6,13-12 |
| Wimbledon | 2019/07/12 15:05 | Rafael Nadal v Roger Federer | 6-7,6-1,3-6,4-6 |
Away History
| US Open | 2019/09/01 16:50 | Grigor Dimitrov v Alex De Minaur | 7-5,6-3,6-4 |
| US Open | 2019/08/30 21:25 | Grigor Dimitrov v Kamil Majchrzak | 7-5,7-6,6-2 |
| US Open | 2019/08/26 18:55 | Andreas Seppi v Grigor Dimitrov | 1-6,7-6,4-6,3-6 |
| ATP Cincinnati | 2019/08/13 15:00 | Grigor Dimitrov v Stan Wawrinka | 7-5,4-6,6-7 |
| ATP Montreal | 2019/08/05 18:55 | Stan Wawrinka v Grigor Dimitrov | 6-4,6-4 |
| ATP Los Cabos | 2019/08/01 01:50 | Grigor Dimitrov v Guido Pella | 4-6,2-6 |
| ATP Los Cabos | 2019/07/31 01:55 | Grigor Dimitrov v Steve Johnson | 7-6,4-6,7-6 |
| ATP Atlanta | 2019/07/24 00:35 | Grigor Dimitrov v Kevin King | 5-7,4-6 |