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Opponent
Rank
05/05/13
Novak Djokovic
1
Madrid Masters
R32
7-6(6) 6-7(8) 6-3
Clay
10/02/23
Carlos Alcaraz
2
Shanghai Masters
R16
5-7 6-2 6-4
Hard
10/04/21
Daniil Medvedev
2
Indian Wells Masters
R16
4-6 6-4 6-3
Hard
03/21/16
Andy Murray
2
Miami Masters
R32
6-7(1) 6-4 6-3
Hard
03/28/24
Carlos Alcaraz
3
Miami
QF
2-6 4-6
Carpet
10/30/23
Daniil Medvedev
3
Paris Masters
R32
6-3 6-7(4) 7-6(2)
Hard
02/08/21
Dominic Thiem
3
Australian Open
R16
6-4 6-4 6-0
Hard
08/26/19
Roger Federer
3
US Open
QF
3-6 6-4 3-6 6-4 6-2
Hard
01/02/17
Milos Raonic
3
Brisbane
SF
7-6(7) 6-2
Hard
06/09/14
Stan Wawrinka
3
Queen's Club
SF
6-2 6-4
Grass
10/14/13
David Ferrer
3
Stockholm
F
2-6 6-3 6-4
Hard
03/29/24
Alexander Zverev
4
Miami
SF
6-4 6(4)-7(7) 6-4
Carpet
09/27/23
Holger Rune
4
Beijing
R16
6-3 7-5
Hard
11/13/17
Dominic Thiem
4
Tour Finals
RR
6-3 5-7 7-5
Hard
10/03/16
Rafael Nadal
4
Beijing
QF
6-2 6-4
Hard
08/15/16
Stan Wawrinka
4
Cincinnati Masters
R16
6-4 6-4
Hard
10/26/20
Stefanos Tsitsipas
5
Vienna
R16
6-7(5) 6-4 6-3
Hard
10/28/19
Dominic Thiem
5
Paris Masters
R16
6-3 6-2
Hard
01/02/17
Kei Nishikori
5
Brisbane
F
6-2 2-6 6-3
Hard
06/23/14
Andy Murray
5
Wimbledon
QF
6-1 7-6(4) 6-2
Grass
09/01/24
Andrey Rublev
6
US Open
R16
3-6 6(3)-7(7) 6-1 6-3 3-6
Hard
10/30/23
Stefanos Tsitsipas
6
Paris Masters
SF
6-3 6-7(1) 7-6(3)
Hard
10/03/16
Milos Raonic
6
Beijing
SF
W/O
Hard
05/11/14
Tomas Berdych
6
Rome Masters
R16
6-7(3) 6-2 6-2
Clay
06/02/24
Hubert Hurkacz
7
Roland Garros
R16
6(5)-7(7) 4-6 6(3)-7(7)
03/26/24
Hubert Hurkacz
7
Miami
R16
3-6 6-3 7(7)-6(3)
Carpet
04/11/22
Casper Ruud
7
Monte Carlo Masters
R16
6-3 7-5
Clay
02/12/18
David Goffin
7
Rotterdam
SF
6-3 0-1 RET
Hard
02/24/14
Andy Murray
7
Acapulco
SF
4-6 7-6(5) 7-6(3)
Hard
03/21/12
Tomas Berdych
7
Miami Masters
R32
6-3 2-6 6-4
Hard
10/24/22
Andrey Rublev
8
Vienna
R16
6-3 6-4
Hard
11/13/17
David Goffin
8
Tour Finals
F
7-5 4-6 6-3
Hard
11/13/17
David Goffin
8
Tour Finals
RR
6-0 6-2
Hard
01/02/17
Dominic Thiem
8
Brisbane
QF
6-3 4-6 6-3
Hard
05/22/23
Taylor Fritz
9
Geneva
SF
3-6 7-5 7-6(2)
Clay
11/13/17
Jack Sock
9
Tour Finals
SF
4-6 6-0 6-3
Hard
05/03/15
Stan Wawrinka
9
Madrid Masters
R16
7-6(5) 3-6 6-3
Clay
04/12/15
Stan Wawrinka
9
Monte Carlo Masters
R16
6-1 6-2
Clay
07/03/23
Frances Tiafoe
10
Wimbledon
R32
6-2 6-3 6-2
Grass
02/13/23
Hubert Hurkacz
10
Rotterdam
R16
7-6(4) 7-6(5)
Hard
04/16/18
David Goffin
10
Monte Carlo Masters
QF
6-4 7-6(5)
Clay
11/13/17
Pablo Carreno Busta
10
Tour Finals
RR
6-1 6-1
Hard
04/14/13
Janko Tipsarevic
10
Monte Carlo Masters
R32
7-6(3) 6-1
Clay