Round 1
Grigor Dimitrov 1 *
Aleksandar Kovacevic
6-4
6-3
6-4
Round 2
Grigor Dimitrov 1 *
Fabian Marozsan
6-0
6-3
6-4
Round 3
Grigor Dimitrov 1 *
Zizou Bergs
6-3
7-6(4)
4-6
6-4
Round 4
Grigor Dimitrov 1 *
Hubert Hurkacz
7-6(5)
6-4
7-6(3)
Quarterfinals
Jannik Sinner 1 *
Grigor Dimitrov
6-2
6-4
7-6(3)
Round 1
Grigor Dimitrov 1 *
Kyrian Jacquet
6-3
6-4
6-2
Round 2
Grigor Dimitrov 1 *
Rinky Hijikata
6-1
6-1
7-6(4)
Round 3
Grigor Dimitrov 1 *
Tallon Griekspoor
6-3
6-3
6-1
Round 4
Grigor Dimitrov 1 *
Andrey Rublev
6-3
7-6(3)
1-6
3-6
6-3
Quarterfinals
Frances Tiafoe 1 *
Grigor Dimitrov
6-3
6-7(5)
6-3
4-1
ret.
Round 1
Grigor Dimitrov 1 *
Andrew Barron (Andy) Murray
4-6
7-5
6-2
Round 2
Grigor Dimitrov 1 *
Daniel Altmaier
6-1
6-2
Quarterfinals
Grigor Dimitrov 1 *
Rinky Hijikata
6-1
6-4
Semifinals
Grigor Dimitrov 1 *
Jordan Thompson
6-3
7-5
Final
Grigor Dimitrov 1 *
Holger Vitus Nodskov Rune
7-6(5)
6-4
Round 1
Round 2
Grigor Dimitrov 1 *
Alejandro Tabilo
6-7(5)
7-6(5)
6-2
Round 3
Grigor Dimitrov 1 *
Yannick Hanfmann
6-1
6-0
Round 4
Grigor Dimitrov 1 *
Hubert Hurkacz
3-6
6-3
7-6(3)
Quarterfinals
Grigor Dimitrov 1 *
Carlos Alcaraz
6-2
6-4
Semifinals
Grigor Dimitrov 1 *
Alexander Zverev
6-4
6-7(4)
6-4
Final
Jannik Sinner 1 *
Grigor Dimitrov
6-3
6-1
Round 1
Round 2
Grigor Dimitrov 1 *
Aleksandar Vukic
6-4
6-3
Round 3
Grigor Dimitrov 1 *
Karen Khachanov
7-6(6)
6-4
Round 4
Grigor Dimitrov 1 *
Carlos Alcaraz
5-7
6-2
6-4
Quarterfinals
Grigor Dimitrov 1 *
Nicolas Jarry
7-6(2)
6-4
Semifinals
Andrey Rublev 1 *
Grigor Dimitrov
7-6(7)
6-3
Round 1
Grigor Dimitrov 1 *
Lorenzo Musetti
6-2
6-7(4)
6-3
Round 2
Grigor Dimitrov 1 *
Daniil Medvedev
6-3
6-7(4)
7-6(2)
Round 3
Grigor Dimitrov 1 *
Alexander Bublik
6-2
6-2
Quarterfinals
Grigor Dimitrov 1 *
Hubert Hurkacz
6-1
4-6
6-4
Semifinals
Grigor Dimitrov 1 *
Stefanos Tsitsipas
6-3
6-7(1)
7-6(3)
Final
Novak Djokovic 1 *
Grigor Dimitrov
6-4
6-3
Round 1
Grigor Dimitrov 1 *
Nikoloz Basilashvili
6-3
2-0
ret.
Round 2
Grigor Dimitrov 1 *
Dusan Lajovic
4-6
6-3
6-2
Round 3
Grigor Dimitrov 1 *
Casper Ruud
6-3
7-5
Quarterfinals
Grigor Dimitrov 1 *
Hubert Hurkacz
6-4
3-6
7-6(2)
Semifinals
Alejandro Davidovich Fokina 1 *
Grigor Dimitrov
6-4
6-7(2)
6-3
Round 1
Grigor Dimitrov 1 *
Marin Cilic
6-4
6-2
7-6(5)
Round 2
Grigor Dimitrov 1 *
Alex Bolt
7-6(1)
6-1
6-2
Round 3
Grigor Dimitrov 1 *
Pablo Carreno Busta
6-0
1-0
ret.
Round 4
Grigor Dimitrov 1 *
Dominic Thiem
6-4
6-4
6-0
Quarterfinals
Aslan Karatsev 1 *
Grigor Dimitrov
2-6
6-4
6-1
6-2
Round 1
Round 2
Grigor Dimitrov 1 *
Daniel Altmaier
6-4
6-2
Round 3
Grigor Dimitrov 1 *
Reilly Opelka
6-3
6-4
Round 4
Grigor Dimitrov 1 *
Daniil Medvedev
4-6
6-4
6-3
Quarterfinals
Grigor Dimitrov 1 *
Hubert Hurkacz
3-6
6-4
7-6(2)
Semifinals
Cameron Norrie 1 *
Grigor Dimitrov
6-2
6-4
Round 1
Grigor Dimitrov 1 *
Andreas Seppi
6-1
6-7(2)
6-4
6-3
Round 2
Grigor Dimitrov 1 *
Borna Coric
w.o.
Round 3
Grigor Dimitrov 1 *
Kamil Majchrzak
7-5
7-6(8)
6-2
Round 4
Grigor Dimitrov 1 *
Alex De Minaur
7-5
6-3
6-4
Quarterfinals
Grigor Dimitrov 1 *
Roger Federer
3-6
6-4
3-6
6-4
6-2
Semifinals
Daniil Medvedev 1 *
Grigor Dimitrov
7-6(5)
6-4
6-3
Round 1
Grigor Dimitrov 1 *
Ugo Humbert
4-6
6-1
6-2
Round 2
Grigor Dimitrov 1 *
David Goffin
7-5
6-3
Round 3
Grigor Dimitrov 1 *
Dominic Thiem
6-3
6-2
Quarterfinals
Grigor Dimitrov 1 *
Cristian Garin
6-2
7-5
Semifinals
Novak Djokovic 1 *
Grigor Dimitrov
7-6(5)
6-4
Round 1
Grigor Dimitrov 1 *
Dennis Novak
6-3
6-2
6-1
Round 2
Grigor Dimitrov 1 *
Mackenzie McDonald
4-6
6-2
6-4
0-6
8-6
Round 3
Grigor Dimitrov 1 *
Andrey Rublev
6-3
4-6
6-4
6-4
Round 4
Grigor Dimitrov 1 *
Nick Kyrgios
7-6(3)
7-6(4)
4-6
7-6(4)
Quarterfinals
Kyle Edmund 1 *
Grigor Dimitrov
6-4
3-6
6-3
6-4
Round 1
Grigor Dimitrov 1 *
Yuichi Sugita
6-4
7-6(5)
Round 2
Grigor Dimitrov 1 *
Filip Krajinovic
7-6(4)
7-5
Quarterfinals
Grigor Dimitrov 1 *
Andrey Rublev
6-3
6-4
Semifinals
Grigor Dimitrov 1 *
David Goffin
6-3
0-1
ret.
Final
Roger Federer 1 *
Grigor Dimitrov
6-2
6-2
Round 1
Grigor Dimitrov 1 *
Christopher O'Connell
7-6(2)
6-3
6-3
Round 2
Grigor Dimitrov 1 *
Hyeon Chung
1-6
6-4
6-4
6-4
Round 3
Grigor Dimitrov 1 *
Richard Gasquet
6-3
6-2
6-4
Round 4
Grigor Dimitrov 1 *
Denis Istomin
2-6
7-6(2)
6-2
6-1
Quarterfinals
Grigor Dimitrov 1 *
David Goffin
6-3
6-2
6-4
Semifinals
Rafael Nadal 1 *
Grigor Dimitrov
6-3
5-7
7-6(5)
6-7(4)
6-4
Round 2
Grigor Dimitrov 1 *
Feliciano López
7-6(5)
6-4
Round 3
Grigor Dimitrov 1 *
Juan Martin Del Potro
6-3
7-5
Quarterfinals
Grigor Dimitrov 1 *
Yuichi Sugita
6-2
6-1
Semifinals
Grigor Dimitrov 1 *
John Robert Isner
7-6(4)
7-6(10)
Final
Grigor Dimitrov 1 *
Nick Kyrgios
6-3
7-5
Round 1
Grigor Dimitrov 1 *
Steve Johnson
6-2
6-3
Round 2
Grigor Dimitrov 1 *
Nicolas Pierre Armand Mahut
6-2
6-4
Quarterfinals
Grigor Dimitrov 1 *
Dominic Thiem
6-3
4-6
6-3
Semifinals
Grigor Dimitrov 1 *
Milos Raonic
7-6(7)
6-2
Final
Grigor Dimitrov 1 *
Kei Nishikori
6-2
2-6
6-3
Round 1
Grigor Dimitrov 1 *
Gilles Simon
6-1
6-3
Round 2
Grigor Dimitrov 1 *
Feliciano López
5-7
6-3
7-6(6)
Round 3
Grigor Dimitrov 1 *
Stanislas Wawrinka
6-4
6-4
Quarterfinals
Grigor Dimitrov 1 *
Steve Johnson
7-6(8)
6-2
Semifinals
Marin Cilic 1 *
Grigor Dimitrov
4-6
6-3
7-5
Round 1
Grigor Dimitrov 1 *
Steve Johnson
7-5
6-7(9)
6-4
Round 2
Grigor Dimitrov 1 *
Lucas Pouille
6-7(3)
7-6(0)
6-4
Quarterfinals
Grigor Dimitrov 1 *
Rafael Nadal
6-2
6-4
Semifinals
Grigor Dimitrov 1 *
Milos Raonic
w.o.
Final
Andrew Barron (Andy) Murray 1 *
Grigor Dimitrov
6-4
7-6(2)
Round 1
Grigor Dimitrov 1 *
Bradley Klahn
6-7(7)
6-4
6-4
6-3
Round 2
Grigor Dimitrov 1 *
Yen-Hsun Lu
6-3
6-3
7-6(11)
Round 3
Grigor Dimitrov 1 *
Milos Raonic
6-3
3-6
6-4
7-6(10)
Round 4
Grigor Dimitrov 1 *
Roberto Bautista-Agut
6-3
3-6
6-2
6-4
Quarterfinals
Rafael Nadal 1 *
Grigor Dimitrov
3-6
7-6(3)
7-6(7)
6-2
Round 1
Grigor Dimitrov 1 *
Ryan Harrison
7-6(1)
6-3
6-2
Round 2
Grigor Dimitrov 1 *
Luke Saville
6-3
6-2
6-4
Round 3
Grigor Dimitrov 1 *
Oleksandr Dolgopolov Jr.
6-7(3)
6-4
2-6
6-4
6-1
Round 4
Grigor Dimitrov 1 *
Leonardo Mayer
6-4
7-6(6)
6-2
Quarterfinals
Grigor Dimitrov 1 *
Andrew Barron (Andy) Murray
6-1
7-6(4)
6-2
Semifinals
Novak Djokovic 1 *
Grigor Dimitrov
6-4
3-6
7-6(2)
7-6(7)
Round 2
Grigor Dimitrov 1 *
James Ward
7-5
6-3
Round 3
Grigor Dimitrov 1 *
Édouard Roger-Vasselin
7-6(3)
6-4
Quarterfinals
Grigor Dimitrov 1 *
Oleksandr Dolgopolov Jr.
w.o.
Semifinals
Grigor Dimitrov 1 *
Stanislas Wawrinka
6-2
6-4
Final
Grigor Dimitrov 1 *
Feliciano López
6-7(8)
7-6(1)
7-6(6)
Round 1
Grigor Dimitrov 1 *
Édouard Roger-Vasselin
4-6
6-3
6-4
Round 2
Grigor Dimitrov 1 *
Ivo Karlovic
7-6(3)
6-4
Round 3
Grigor Dimitrov 1 *
Tomas Berdych
6-7(3)
6-2
6-2
Quarterfinals
Grigor Dimitrov 1 *
Thomas Mario (Tommy) Haas
6-2
0-0
ret.
Semifinals
Rafael Nadal 1 *
Grigor Dimitrov
6-2
6-2
Round 1
Grigor Dimitrov 1 *
Marinko Matosevic
7-5
6-1
Round 2
Grigor Dimitrov 1 *
Marcos Baghdatis
6-1
6-4
Quarterfinals
Grigor Dimitrov 1 *
Ernests Gulbis
4-6
7-6(2)
7-5
Semifinals
Grigor Dimitrov 1 *
Andrew Barron (Andy) Murray
4-6
7-6(5)
7-6(3)
Final
Grigor Dimitrov 1 *
Kevin Anderson
7-6(1)
3-6
7-6(5)
Round 1
Grigor Dimitrov 1 *
Brian Baker
6-3
7-6(8)
Round 2
Grigor Dimitrov 1 *
Milos Raonic
6-3
6-4
Quarterfinals
Grigor Dimitrov 1 *
Jurgen Melzer
6-3
6-2
Semifinals
Grigor Dimitrov 1 *
Marcos Baghdatis
6-3
5-7
7-6(5)
Final
Andrew Barron (Andy) Murray 1 *
Grigor Dimitrov
7-6(0)
6-4
Round 1
Grigor Dimitrov 1 *
Marius Copil
6-3
6-4
Round 2
Grigor Dimitrov 1 *
Jan Lennard Struff
6-1
6-3
Quarterfinals
Grigor Dimitrov 1 *
Kenny De Schepper
6-4
6-2
Semifinals
Grigor Dimitrov 1 *
Benoit Paire
4-6
6-2
6-2
Final
Grigor Dimitrov 1 *
David Ferrer
2-6
6-3
6-4
Round 1
Grigor Dimitrov 1 *
Robert Thomas (Bobby) Reynolds
6-3
7-5
Round 2
Grigor Dimitrov 1 *
Gilles Muller
7-6(1)
6-4
Round 3
Grigor Dimitrov 1 *
Nicolas Pierre Armand Mahut
7-6(3)
6-4
Quarterfinals
Grigor Dimitrov 1 *
Kevin Anderson
4-6
6-4
6-3
Semifinals
David Pablo Nalbandian 1 *
Grigor Dimitrov
6-4
6-4