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Opponent
Rank
11/15/21
Novak Djokovic
1
Tour Finals
SF
7-6(4) 4-6 6-3
Hard
07/24/21
Novak Djokovic
1
Tokyo Olympics
SF
1-6 6-3 6-1
Hard
11/11/19
Rafael Nadal
1
Tour Finals
RR
6-2 6-4
Hard
11/12/18
Novak Djokovic
1
Tour Finals
F
6-4 6-3
Hard
11/13/23
Carlos Alcaraz
2
Tour Finals
RR
6-7(3) 6-3 6-4
Hard
11/15/21
Daniil Medvedev
2
Tour Finals
F
6-4 6-4
Hard
05/03/21
Rafael Nadal
2
Madrid Masters
QF
6-4 6-4
Clay
11/02/20
Rafael Nadal
2
Paris Masters
SF
6-4 7-5
Hard
05/15/17
Novak Djokovic
2
Rome Masters
F
6-4 6-3
Clay
01/24/24
Carlos Alcaraz
3
Australian Open
QF
6-1 6-3 6(2)-7(7) 6-4
Hard
08/14/23
Daniil Medvedev
3
Cincinnati Masters
R16
6-4 5-7 6-4
Hard
08/16/21
Stefanos Tsitsipas
3
Cincinnati Masters
SF
6-4 3-6 7-6(4)
Hard
10/07/19
Roger Federer
3
Shanghai Masters
QF
6-3 6-7(7) 6-3
Hard
11/12/18
Roger Federer
3
Tour Finals
SF
7-5 7-6(5)
Hard
08/07/17
Roger Federer
3
Canada Masters
F
6-3 6-4
Hard
03/20/17
Stan Wawrinka
3
Miami Masters
R16
4-6 6-2 6-1
Hard
09/19/16
Stan Wawrinka
3
St. Petersburg
F
6-2 3-6 7-5
Hard
06/13/16
Roger Federer
3
Halle
SF
7-6(4) 5-7 6-3
Grass
05/03/21
Dominic Thiem
4
Madrid Masters
SF
6-3 6-4
Clay
11/11/19
Daniil Medvedev
4
Tour Finals
RR
6-4 7-6(4)
Hard
11/13/23
Andrey Rublev
5
Tour Finals
RR
6-4 6-4
Hard
05/02/22
Stefanos Tsitsipas
5
Madrid Masters
SF
6-4 3-6 6-2
Clay
03/15/21
Stefanos Tsitsipas
5
Acapulco
F
6-4 7-6(3)
Hard
05/14/18
Marin Cilic
5
Rome Masters
SF
7-6(13) 7-5
Clay
11/13/17
Marin Cilic
5
Tour Finals
RR
6-4 3-6 6-4
Hard
08/28/23
Jannik Sinner
6
US Open
R16
6-4 3-6 6-2 4-6 6-3
Hard
05/23/22
Carlos Alcaraz
6
Roland Garros
QF
6-4 6-4 4-6 7-6(7)
Clay
05/15/17
Milos Raonic
6
Rome Masters
QF
7-6(4) 6-1
Clay
01/07/24
Hubert Hurkacz
7
United Cup
7(7)-6(3) 6(6)-7(8) 4-6
Hard
11/15/21
Matteo Berrettini
7
Tour Finals
RR
7-6(7) 1-0 RET
Hard
08/16/21
Andrey Rublev
7
Cincinnati Masters
F
6-2 6-3
Hard
11/12/18
Marin Cilic
7
Tour Finals
RR
7-6(5) 7-6(1)
Hard
05/07/18
Dominic Thiem
7
Madrid Masters
F
6-4 6-4
Clay
05/08/17
Marin Cilic
7
Madrid Masters
R32
6-7(3) 6-3 6-4
Clay
06/07/24
Casper Ruud
8
Roland Garros
SF
6-2 2-6 4-6 2-6
11/01/21
Casper Ruud
8
Paris Masters
QF
7-5 6-4
Hard
06/05/24
Alex De Minaur
9
Roland Garros
QF
6-4 7(7)-6(5) 6-4
03/12/24
Alex De Minaur
9
Indian Wells
R16
5-7 6-2 6-3
Hard
11/15/21
Hubert Hurkacz
9
Tour Finals
RR
6-2 6-4
Hard
11/16/20
Diego Schwartzman
9
Tour Finals
RR
6-3 4-6 6-3
Hard
10/19/20
Diego Schwartzman
9
Cologne 2
F
6-2 6-1
Hard
09/21/18
Kevin Anderson
9
Laver Cup
RR
6-7(3) 7-5 [10-7]
Hard
05/07/18
John Isner
9
Madrid Masters
QF
6-4 7-5
Clay
07/31/17
Kei Nishikori
9
Washington
SF
6-3 6-4
Hard
09/19/16
Tomas Berdych
9
St. Petersburg
SF
6-4 6-4
Hard
05/02/22
Felix Auger-Aliassime
10
Madrid Masters
QF
6-3 7-5
Clay
05/03/21
Matteo Berrettini
10
Madrid Masters
F
6-7(8) 6-4 6-3
Clay
11/12/18
John Isner
10
Tour Finals
RR
7-6(5) 6-3
Hard
09/21/18
John Isner
10
Laver Cup
RR
3-6 7-6(6) [10-7]
Hard
05/14/18
David Goffin
10
Rome Masters
QF
6-4 3-6 6-3
Clay
10/03/16
Dominic Thiem
10
Beijing
R32
4-6 6-1 6-3
Hard