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Match result
|
Previous games between the teams to this day
| Tournament | Round | Player 1 | Player 2 | Date | Set1 | Set2 | Set3 | Set4 | Set5 | HDC | Surface | |
| 1R |
|
Tipsarevic J. (5.50) | Dimitrov G. (1.20) | 05/26/19 | 3-6 | 0-6 | 6-3 | 7-6(4) | 4-6 | +7 | Clay | |
| 1R |
|
Dimitrov G. (1.07) | Tipsarevic J. (12.88) | 01/14/19 | 4-6 | 6-3 | 6-1 | 6-4 | +8 | Hard | ||
| 1R |
|
Dimitrov G. (1.27) | Tipsarevic J. (4.50) | 06/14/16 | 6-7(6) | 6-4 | 3-6 | +2 | Grass | |||
| 2R |
|
Tipsarevic J. (1.85) | Dimitrov G. (2.20) | 04/16/13 | 6-7(3) | 1-6 | +6 | Clay | ||||
| 4R |
|
Dimitrov G. (3.85) | Tipsarevic J. (1.35) | 03/27/12 | 6-7(3) | 2-6 | +5 | Hard |
ℹ️ The handicap indicated in the HDC column refers to the winner
