Milos Raonic
| Milos Raonic | |
|---|---|
 | |
| Birthdate | December 27, 1990 |
| Birthplace | Titograd, SFR Yugoslavia |
| From | Thornhill, Ontario, Canada |
| Residence | Monte-Carlo, Monaco |
| Height | 6’5” (1,96m) |
| Style of play | Right-handed (two-handed backhand) |
| Turned pro | 2008 |
| Best ATP singles ranking | No. 3 (November 21, 2016) |
| Best ATP doubles ranking | No. 103 (June 10, 2013) |
| Profile on CdnTennis.ca | |
Biography
Milos Raonic (born December 27, 1990 in Titograd, SR Montenegro, SFR Yugoslavia) is a Canadian professional tennis player. He reached a career-high ATP singles ranking of No. 3 on November 21, 2016 and a career-high ATP doubles ranking of No. 103 on June 10, 2013.
His career highlights include a Grand Slam final at the 2016 Wimbledon Championships; two Grand Slam semifinals at the 2014 Wimbledon Championships and 2016 Australian Open; and four ATP World Tour Masters 1000 finals at the 2013 Canadian Open, 2014 Paris Masters, 2016 Indian Wells Masters and 2020 Cincinnati Masters. Raonic first gained international acclaim by reaching the fourth round of the 2011 Australian Open as a qualifier, being referred to as "the real deal", "a new star", part of "a new generation", and "a future superstar". Coupled with his first ATP World Tour title three weeks later, his world ranking rose from No. 152 to No. 37 in one month. He was awarded the 2011 ATP Newcomer of the Year. Raonic is the first player born in the 1990s to win an ATP World Tour title, to be ranked in the top 10, and to qualify for the ATP World Tour Finals. He has eight ATP World Tour titles. Raonic is the most successful Canadian singles player in history. He became the highest-ranked Canadian male ever on February 21, 2011, when he reached No. 37. His career-high No. 3 ranking is the highest by a Canadian man or woman. He is the first Canadian male in the Open Era to reach the Australian Open semifinals, the French Open quarterfinals, and the Wimbledon final. He has more ATP World Tour titles and finals appearances in the Open Era than all other Canadian men combined. Raonic was named Male Player of the Year by Tennis Canada eight times (2011, 2012, 2013, 2014, 2015, 2016, 2018, 2020) and received the Lionel Conacher Award as the Canadian male athlete of the year in 2013 and 2014.
Raonic is of Serb heritage. Prompted by the political unrest in the Balkans, and seeking more professional opportunities, his family moved to Canada in 1994 when he was three, settling in Brampton, Ontario. His parents are both engineers; his father, Dušan, holds a Ph.D. in electrical engineering, while his mother, Vesna, has degrees in mechanical and computer engineering, including a master's. He has two siblings, both significantly older: his sister, Jelena, has a master's degree in international trade and finance and is eleven years older, while his brother, Momir, has a degree in information technology and business and is nine years older. Raonic's uncle, Branimir Gvozdenović, is a politician in the Government of Montenegro, where he has served as Deputy Prime Minister. His first, brief introduction to tennis came at age six or seven with a week-long tennis camp at the Bramalea Tennis Club in Brampton, followed by weekly hour-long group sessions led by tennis coach Steve Gibson, who recognized his potential. He moved to nearby Thornhill, Ontario soon after, and one or two years passed before he asked his parents if he could play again. His father sought out coach Casey Curtis at the Blackmore Tennis Club in Richmond Hill, Ontario. Raonic and Curtis worked together "twice a day, almost every day, for the next nine years." Late in 2007, at the age of 16, Raonic moved to Montréal as one of the first group of players at Tennis Canada's new National Tennis Centre, thus marking the end of his formal relationship with Curtis, and was a member until 2010.
Grand Slam finals
Singles: 1 (1 runner-up)
| Result | Year | Tournament | Surface | Opponent | Score |
|---|---|---|---|---|---|
| Loss | 2016 | Wimbledon | Grass | Andy Murray (GBR) | 4–6, 6–7(3–7), 6–7(2–7) |
Other significant finals
ATP Masters 1000 finals
Singles: 4 (4 runners-up)
| Result | Year | Tournament | Surface | Opponent | Score |
|---|---|---|---|---|---|
| Loss | 2013 | Montréal | Hard | Rafael Nadal (ESP) | 2–6, 2–6 |
| Loss | 2014 | Paris | Hard (i) | Novak Djokovic (SRB) | 2–6, 3–6 |
| Loss | 2016 | Indian Wells | Hard | Novak Djokovic (SRB) | 2–6, 0–6 |
| Loss | 2020 | Cincinnati | Hard | Novak Djokovic (SRB) | 6–1, 3–6, 4–6 |
ATP career finals
Singles: 23 (8 titles, 15 runners-up)
|
|
| Result | W–L | Date | Tournament | Tier | Surface | Opponent | Score |
|---|---|---|---|---|---|---|---|
| Win | 1–0 | Feb 2011 | Pacific Coast Championships, United States | 250 Series | Hard (i) | Fernando Verdasco (ESP) | 7–6(8–6), 7–6(7–5) |
| Loss | 1–1 | Feb 2011 | Memphis Open, United States | 500 Series | Hard (i) | Andy Roddick (USA) | 6–7(7–9), 7–6(13–11), 5–7 |
| Win | 2–1 | Jan 2012 | Chennai Open, India | 250 Series | Hard | Janko Tipsarević (SRB) | 6–7(4–7), 7–6(7–4), 7–6(7–4) |
| Win | 3–1 | Feb 2012 | Pacific Coast Championships, United States (2) | 250 Series | Hard (i) | Denis Istomin (UZB) | 7–6(7–3), 6–2 |
| Loss | 3–2 | Feb 2012 | Memphis Open, United States | 500 Series | Hard (i) | Jürgen Melzer (AUT) | 5–7, 6–7(4–7) |
| Loss | 3–3 | Oct 2012 | Japan Open, Japan | 500 Series | Hard | Kei Nishikori (JPN) | 6–7(5–7), 6–3, 0–6 |
| Win | 4–3 | Feb 2013 | Pacific Coast Championships, United States (3) | 250 Series | Hard (i) | Tommy Haas (GER) | 6–4, 6–3 |
| Loss | 4–4 | Aug 2013 | Canadian Open, Canada | Masters 1000 | Hard | Rafael Nadal (ESP) | 2–6, 2–6 |
| Win | 5–4 | Sep 2013 | Thailand Open, Thailand | 250 Series | Hard (i) | Tomáš Berdych (CZE) | 7–6(7–4), 6–3 |
| Loss | 5–5 | Oct 2013 | Japan Open, Japan | 500 Series | Hard | Juan Martín del Potro (ARG) | 6–7(5–7), 5–7 |
| Win | 6–5 | Aug 2014 | Washington Open, United States | 500 Series | Hard | Vasek Pospisil (CAN) | 6–1, 6–4 |
| Loss | 6–6 | Oct 2014 | Japan Open, Japan | 500 Series | Hard | Kei Nishikori (JPN) | 6–7(5–7), 6–4, 4–6 |
| Loss | 6–7 | Nov 2014 | Paris Masters, France | Masters 1000 | Hard (i) | Novak Djokovic (SRB) | 2–6, 3–6 |
| Loss | 6–8 | Jan 2015 | Brisbane International, Australia | 250 Series | Hard | Roger Federer (SUI) | 4–6, 7–6(7–2), 4–6 |
| Win | 7–8 | Sep 2015 | St. Petersburg Open, Russia | 250 Series | Hard (i) | João Sousa (POR) | 6–3, 3–6, 6–3 |
| Win | 8–8 | Jan 2016 | Brisbane International, Australia | 250 Series | Hard | Roger Federer (SUI) | 6–4, 6–4 |
| Loss | 8–9 | Mar 2016 | Indian Wells Masters, United States | Masters 1000 | Hard | Novak Djokovic (SRB) | 2–6, 0–6 |
| Loss | 8–10 | Jun 2016 | Queen's Club Championships, United Kingdom | 500 Series | Grass | Andy Murray (GBR) | 7–6(7–5), 4–6, 3–6 |
| Loss | 8–11 | Jul 2016 | Wimbledon, United Kingdom | Grand Slam | Grass | Andy Murray (GBR) | 4–6, 6–7(3–7), 6–7(2–7) |
| Loss | 8–12 | Feb 2017 | Delray Beach Open, United States | 250 Series | Hard | Jack Sock (USA) | Walkover |
| Loss | 8–13 | May 2017 | Istanbul Open, Turkey | 250 Series | Clay | Marin Čilić (CRO) | 6–7(3–7), 3–6 |
| Loss | 8–14 | Jun 2018 | Stuttgart Open, Germany | 250 Series | Grass | Roger Federer (SUI) | 4–6, 6–7(3–7) |
| Loss | 8–15 | Aug 2020 | Cincinnati Masters, United States | Masters 1000 | Hard | Novak Djokovic (SRB) | 6–1, 3–6, 4–6 |
Doubles: 1 (1 runner-up)
|
|
| Result | W–L | Date | Tournament | Tier | Surface | Partner | Opponents | Score |
|---|---|---|---|---|---|---|---|---|
| Loss | 0–1 | Jun 2011 | Halle Open, Germany | 250 Series | Grass | Robin Haase (NED) | Rohan Bopanna (IND) Aisam-ul-Haq Qureshi (PAK) |
6–7(8–10), 6–3, [9–11] |
Other finals
Team competitions: 1 (1 runner-up)
| Result | Date | Tournament | Surface | Team | Partners | Opponent team | Opponent players | Score |
|---|---|---|---|---|---|---|---|---|
| Loss | Sep 2019 | Laver Cup, Geneva, Switzerland | Hard (i) | Team World | Taylor Fritz (USA) John Isner (USA) Nick Kyrgios (AUS) Denis Shapovalov (CAN) Jack Sock (USA) |
Team Europe | Roger Federer (SUI) Fabio Fognini (ITA) Rafael Nadal (ESP) Dominic Thiem (AUT) Stefanos Tsitsipas (GRE) Alexander Zverev (GER) |
11–13 |
ATP Challenger Tour finals
Singles: 1 (1 runner-up)
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|
| Result | W–L | Date | Tournament | Tier | Surface | Opponent | Score |
|---|---|---|---|---|---|---|---|
| Loss | 0–1 | Aug 2010 | Granby, Canada | $50,000 | Hard | Tobias Kamke (GER) | 3–6, 6–7(4–7) |
Doubles: 1 (1 title)
|
|
| Result | W–L | Date | Tournament | Tier | Surface | Partner | Opponents | Score |
|---|---|---|---|---|---|---|---|---|
| Win | 1–0 | Nov 2008 | Rimouski, Canada | $35,000 | Hard (i) | Vasek Pospisil (CAN) | Kristian Pless (DEN) Michael Ryderstedt (SWE) |
5–7, 6–4, [10–6] |
ITF Circuit finals
Singles: 7 (4 titles, 3 runners-up)
|
|
| Result | W–L | Date | Tournament | Tier | Surface | Opponent | Score |
|---|---|---|---|---|---|---|---|
| Loss | 0–1 | Mar 2008 | Canada F3, Sherbrooke | $10,000 | Hard (i) | Enrico Iannuzzi (ITA) | 5–7, 6–7(4–7) |
| Win | 1–1 | Mar 2009 | Canada F2, Montréal | $10,000 | Hard (i) | Grégoire Burquier (FRA) | 6–3, 6–4 |
| Loss | 1–2 | Aug 2009 | Thailand F1, Nonthaburi | $10,000 | Hard | Kittipong Wachiramanowong (THA) | 6–3, 4–6, 3–6 |
| Win | 2–2 | Aug 2009 | Thailand F2, Nonthaburi | $10,000 | Hard | Laurent Rochette (FRA) | 6–7(1–7), 7–6(7–2), 7–5 |
| Loss | 2–3 | Mar 2010 | Canada F3, Sherbrooke | $10,000 | Hard (i) | Vasek Pospisil (CAN) | 4–6, 6–4, 3–6 |
| Win | 3–3 | Apr 2010 | Korea F2, Daegu | $15,000 | Hard | Hiroki Kondo (JPN) | 6–1, 6–1 |
| Win | 4–3 | May 2010 | Korea F4, Gimcheon | $15,000 | Hard | Max Raditschnigg (AUT) | 6–4, 6–4 |
Doubles: 8 (5 titles, 3 runners-up)
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|
| Result | W–L | Date | Tournament | Tier | Surface | Partner | Opponents | Score |
|---|---|---|---|---|---|---|---|---|
| Win | 1–0 | Mar 2008 | Canada F1, Gatineau | $10,000 | Hard (i) | Milan Pokrajac (CAN) | Christopher Klingemann (USA) Thomas Schoeck (GER) |
7–6(7–2), 6–7(3–7), [10–8] |
| Loss | 1–1 | Mar 2008 | Canada F2, Montréal | $10,000 | Hard (i) | Milan Pokrajac (CAN) | Travis Rettenmaier (USA) Rylan Rizza (USA) |
6–7(5–7), 6–7(4–7) |
| Loss | 1–2 | Feb 2009 | Croatia F2, Zagreb | $15,000 | Hard (i) | Érik Chvojka (CAN) | Victor Ioniță (ROU) Denis Matsukevich (RUS) |
4–6, 5–7 |
| Win | 2–2 | Apr 2009 | USA F7, Mobile | $15,000 | Hard | Philip Bester (CAN) | Lester Cook (USA) Treat Huey (PHI) |
6–3, 1–6, [10–5] |
| Win | 3–2 | Jun 2009 | Slovenia F3, Koper | $10,000 | Clay | Denys Molchanov (UKR) | Roman Jebavý (CZE) David Novak (CZE) |
7–5, 5–7, [10–5] |
| Win | 4–2 | Jul 2009 | USA F17, Peoria | $10,000 | Clay | Vasek Pospisil (CAN) | Matt Reid (AUS) Denis Zivkovic (USA) |
6–3, 6–4 |
| Win | 5–2 | Aug 2009 | Thailand F1, Nonthaburi | $10,000 | Hard | Nikolaus Moser (AUT) | Satoshi Iwabuchi (JPN) Gouichi Motomura (JPN) |
0–6, 7–6(7–2), [10–3] |
| Loss | 5–3 | Mar 2010 | Canada F3, Sherbrooke | $10,000 | Hard (i) | Vasek Pospisil (CAN) | Cory Parr (USA) Todd Paul (USA) |
4–6, 4–6 |
Singles performance timeline
This table is current as of August 2, 2021.
| Tournament | 2008 | 2009 | 2010 | 2011 | 2012 | 2013 | 2014 | 2015 | 2016 | 2017 | 2018 | 2019 | 2020 | 2021 | 2022 | 2023 | SR | W–L | Win % |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Grand Slam tournaments | |||||||||||||||||||
| Australian Open | A | A | A | 4R | 3R | 4R | 3R | QF | SF | QF | 1R | QF | QF | 4R | A | A | 0 / 11 | 34–11 | 76% |
| French Open | A | A | A | 1R | 3R | 3R | QF | A | 4R | 4R | A | A | A | A | A | A | 0 / 6 | 14–6 | 70% |
| Wimbledon | A | A | A | 2R | 2R | 2R | SF | 3R | F | QF | QF | 4R | NH | A | A | 0 / 9 | 27–9 | 75% | |
| US Open | A | A | 1R | A | 4R | 4R | 4R | 3R | 2R | A | 4R | A | 2R | A | A | 0 / 8 | 16–8 | 67% | |
| Win–Loss | 0–0 | 0–0 | 0–1 | 4–3 | 8–4 | 9–4 | 14–4 | 8–3 | 15–4 | 11–3 | 7–3 | 7–2 | 5–2 | 3–1 | 0–0 | 0–0 | 0 / 34 | 91–34 | 73% |
| Year-end championships | |||||||||||||||||||
| ATP Finals | Did Not Qualify | RR | DNQ | SF | Did Not Qualify | 0 / 2 | 2–4 | 33% | |||||||||||
| ATP Masters Series / ATP Masters 1000 tournaments | |||||||||||||||||||
| Indian Wells | A | A | A | 3R | 3R | 4R | QF | SF | F | A | SF | SF | NH | A | A | A | 0 / 8 | 23–8 | 74% |
| Miami | A | A | A | 2R | 3R | 3R | QF | 4R | QF | 3R | QF | 3R | NH | 4R | A | A | 0 / 10 | 16–7 | 70% |
| Monte-Carlo | A | A | A | 3R | 1R | 2R | QF | QF | QF | A | 3R | A | NH | A | A | A | 0 / 7 | 12–6 | 67% |
| Madrid | A | A | A | 1R | 2R | 2R | 3R | QF | QF | 3R | 3R | A | NH | A | A | A | 0 / 8 | 11–8 | 58% |
| Rome | A | A | A | 1R | 1R | 1R | SF | A | 2R | QF | A | A | 2R | A | A | A | 0 / 7 | 7–7 | 50% |
| Canada | Q1 | 1R | 1R | A | QF | F | QF | 2R | QF | 2R | 2R | 2R | NH | A | A | 0 / 10 | 12–10 | 55% | |
| Cincinnati | A | A | A | A | QF | 3R | SF | 1R | SF | A | QF | A | F | A | A | 0 / 7 | 19–7 | 73% | |
| Shanghai | NH | A | A | 2R | 2R | 3R | 2R | 3R | 3R | A | 1R | A | Not Held | 0 / 7 | 7–7 | 50% | |||
| Paris | A | A | A | 1R | 3R | 3R | F | A | SF | A | 2R | 2R | SF | A | A | 0 / 8 | 15–6 | 71% | |
| Win–Loss | 0–0 | 0–1 | 0–1 | 5–7 | 9–8 | 14–8 | 21–9 | 12–7 | 24–8 | 4–3 | 15–6 | 5–3 | 10–3 | 2–1 | 0–0 | 0–0 | 0 / 71 | 121–65 | 65% |
| Former ATP Masters Series / ATP Masters 1000 tournaments | |||||||||||||||||||
| Hamburg | A | Not Masters 1000 | 0 / 0 | 0–0 | – | ||||||||||||||
| Win–Loss | 0–0 | 0–0 | 0–0 | 0–0 | 0–0 | 0–0 | 0–0 | 0–0 | 0–0 | 0–0 | 0–0 | 0–0 | 0–0 | 0–0 | 0–0 | 0–0 | 0 / 0 | 0–0 | – |
| National representation | |||||||||||||||||||
| Olympic Games | A | Not Held | 2R | Not Held | A | Not Held | A | Not Held | 0 / 1 | 1–1 | 50% | ||||||||
| Davis Cup | A | A | AZ1 | PO | 1R | SF | PO | 1R | A | A | PO | A | NH | A | A | 0 / 3 | 16–5 | 76% | |
| ATP Cup | Not Held | A | RR | A | NH | 0 / 1 | 1–1 | 50% | |||||||||||
| Career statistics | |||||||||||||||||||
| 2008 | 2009 | 2010 | 2011 | 2012 | 2013 | 2014 | 2015 | 2016 | 2017 | 2018 | 2019 | 2020 | 2021 | 2022 | 2023 | SR | W–L | Win % | |
| Tournaments | 0 | 1 | 4 | 19 | 23 | 23 | 20 | 16 | 19 | 14 | 18 | 13 | 10 | 5 | 0 | 0 | 185 | ||
| Titles | 0 | 0 | 0 | 1 | 2 | 2 | 1 | 1 | 1 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 8 | ||
| Finals | 0 | 0 | 0 | 2 | 4 | 4 | 3 | 2 | 4 | 2 | 1 | 0 | 1 | 0 | 0 | 0 | 23 | ||
| Hardcourt Win–Loss | 0–0 | 0–1 | 4–4 | 19–11 | 33–11 | 36–12 | 33–13 | 25–12 | 32–11 | 14–5 | 19–12 | 14–12 | 22–8 | 7–5 | 0–0 | 0–0 | 8 / 127 | 258–117 | 69% |
| Clay Win–Loss | 0–0 | 0–0 | 0–2 | 9–6 | 7–5 | 8–6 | 11–5 | 4–2 | 10–4 | 11–5 | 4–1 | 0–0 | 1–1 | 0–0 | 0–0 | 0–0 | 0 / 35 | 65–37 | 64% |
| Grass Win–Loss | 0–0 | 0–0 | 0–0 | 3–2 | 5–4 | 1–3 | 5–2 | 4–2 | 10–2 | 4–2 | 9–2 | 8–2 | 0–0 | 0–0 | 0–0 | 0–0 | 0 / 23 | 49–21 | 70% |
| Overall Win–Loss | 0–0 | 0–1 | 4–6 | 31–19 | 45–20 | 45–21 | 49–20 | 33–16 | 52–17 | 29–12 | 32–15 | 22–14 | 23–9 | 7–5 | 0–0 | 0–0 | 8 / 185 | 372–175 | 68% |
| Win % | – | 0% | 40% | 62% | 69% | 68% | 71% | 67% | 75% | 71% | 68% | 61% | 72% | 58% | – | – | 68.01% | ||
| Year-end ranking | 923 | 380 | 156 | 31 | 13 | 11 | 8 | 14 | 3 | 24 | 18 | 31 | 14 | 70 | – | – | |||
Notes
- NB The ATP Masters 1000 tournament in Cincinnati was played in New York City, the French Open was played in September and after the US Open, and the Italian Open was also played in September and after the ATP Masters 1000 in New York City/Cincinnati, and the 2020 Olympic Games were postponed to 2021 due to the COVID-19 pandemic in 2020.
- NB The ATP Masters 1000 tournament in Indian Wells was played in October and after the tournament in Cincinnati due to the COVID-19 pandemic in 2021.
Wins over top-10 opponents
Raonic has a 30–67 (31%) record against players who were, at the time the match was played, ranked in the top 10.
| Season | 2008 | 2009 | 2010 | 2011 | 2012 | 2013 | 2014 | 2015 | 2016 | 2017 | 2018 | 2019 | 2020 | 2021 | 2022 | 2023 | Total |
| Wins | 0 | 0 | 0 | 3 | 6 | 3 | 3 | 2 | 8 | 1 | 1 | 1 | 2 | 0 | 0 | 0 | 30 |
| No. | Opponent | Rank | Event | Surface | Round | Score | Raonic Rank | |
|---|---|---|---|---|---|---|---|---|
| 2011 | ||||||||
| 1. | Mikhail Youzhny (RUS) | 10 | Australian Open, Australia | Hard | 3R | 6–4, 7–5, 4–6, 6–4 | 152 | |
| 2. | Fernando Verdasco (ESP) | 9 | Pacific Coast Championships, United States | Hard (i) | F | 7–6(8–6), 7–6(7–5) | 84 | |
| 3. | Fernando Verdasco (ESP) | 9 | Memphis Open, United States | Hard (i) | 1R | 6–4, 3–6, 7–6(7–5) | 59 | |
| 2012 | ||||||||
| 4. | Nicolás Almagro (ESP) | 10 | Chennai Open, India | Hard | SF | 6–4, 6–4 | 31 | |
| 5. | Janko Tipsarević (SRB) | 9 | Chennai Open, India | Hard | F | 6–7(4–7), 7–6(7–4), 7–6(7–4) | 31 | |
| 6. | Andy Murray (GBR) | 4 | Barcelona Open, Spain | Clay | QF | 6–4, 7–6(7–3) | 25 | |
| 7. | Tomáš Berdych (CZE) | 7 | Cincinnati Masters, United States | Hard | 3R | 6–4, 2–6, 6–2 | 19 | |
| 8. | Janko Tipsarević (SRB) | 9 | Japan Open, Japan | Hard | QF | 6–7(5–7), 6–2, 7–6(9–7) | 15 | |
| 9. | Andy Murray (GBR) | 3 | Japan Open, Japan | Hard | SF | 6–3, 6–7(5–7), 7–6(7–4) | 15 | |
| 2013 | ||||||||
| 10. | Juan Martín del Potro (ARG) | 7 | Canadian Open, Canada | Hard | 3R | 7–5, 6–4 | 13 | |
| 11. | Richard Gasquet (FRA) | 9 | Thailand Open, Thailand | Hard (i) | SF | 3–6, 7–5, 6–4 | 11 | |
| 12. | Tomáš Berdych (CZE) | 6 | Thailand Open, Thailand | Hard (i) | F | 7–6(7–4), 6–3 | 11 | |
| 2014 | ||||||||
| 13. | Andy Murray (GBR) | 6 | Indian Wells Masters, United States | Hard | 4R | 4–6, 7–5, 6–3 | 11 | |
| 14. | Roger Federer (SUI) | 2 | Paris Masters, France | Hard (i) | QF | 7–6(7–5), 7–5 | 10 | |
| 15. | Tomáš Berdych (CZE) | 5 | Paris Masters, France | Hard (i) | SF | 6–3, 3–6, 7–5 | 10 | |
| 2015 | ||||||||
| 16. | Kei Nishikori (JPN) | 5 | Brisbane International, Australia | Hard | SF | 6–7(4–7), 7–6(7–4), 7–6(7–4) | 8 | |
| 17. | Rafael Nadal (ESP) | 3 | Indian Wells Masters, United States | Hard | QF | 4–6, 7–6(12–10), 7–5 | 6 | |
| 2016 | ||||||||
| 18. | Roger Federer (SUI) | 3 | Brisbane International, Australia | Hard | F | 6–4, 6–4 | 14 | |
| 19. | Stan Wawrinka (SUI) | 4 | Australian Open, Australia | Hard | 4R | 6–4, 6–3, 5–7, 4–6, 6–3 | 14 | |
| 20. | Tomáš Berdych (CZE) | 7 | Indian Wells Masters, United States | Hard | 4R | 6–4, 7–6(9–7) | 14 | |
| 21. | Jo-Wilfried Tsonga (FRA) | 7 | Madrid Open, Spain | Clay | 3R | 6–4, 6–4 | 10 | |
| 22. | Roger Federer (SUI) | 3 | Wimbledon, United Kingdom | Grass | SF | 6–3, 6–7(3–7), 4–6, 7–5, 6–3 | 7 | |
| 23. | Dominic Thiem (AUT) | 9 | Cincinnati Masters, United States | Hard | QF | 6–3, 6–4 | 6 | |
| 24. | Gaël Monfils (FRA) | 6 | ATP Finals, United Kingdom | Hard (i) | RR | 6–3, 6–4 | 4 | |
| 25. | Dominic Thiem (AUT) | 9 | ATP Finals, United Kingdom | Hard (i) | RR | 7–6(7–5), 6–3 | 4 | |
| 2017 | ||||||||
| 26. | Rafael Nadal (ESP) | 9 | Brisbane International, Australia | Hard | QF | 4–6, 6–3, 6–4 | 3 | |
| 2018 | ||||||||
| 27. | Grigor Dimitrov (BUL) | 4 | Madrid Open, Spain | Clay | 2R | 7–5, 3–6, 6–3 | 24 | |
| 2019 | ||||||||
| 28. | Alexander Zverev Jr. (GER) | 4 | Australian Open, Australia | Hard | 4R | 6–1, 6–1, 7–6(7–5) | 17 | |
| 2020 | ||||||||
| 29. | Stefanos Tsitsipas (GRE) | 6 | Australian Open, Australia | Hard | 3R | 7–5, 6–4, 7–6(7–2) | 35 | |
| 30. | Stefanos Tsitsipas (GRE) | 6 | Cincinnati Masters, United States | Hard | SF | 7–6(7–5), 6–3 | 30 | |