H2H data updated: 2026-09-01 00:00 UTC

Grigor Dimitrov vs Milos Raonic H2H: 5-2

Grigor Dimitrov holds a 5–2 lead over Milos Raonic in their ATP head-to-head. Across 7 main-draw meetings, Grigor Dimitrov leads 5–1 on hard courts, while Milos Raonic leads 1–0 on clay. Most recently, Grigor Dimitrov won the 2020 Antwerp quarterfinal W/O.

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Grigor Dimitrov
Bulgaria Age 35 Right-Handed 191 cm / 6'3"
H2H
5 – 2
7 main draw meetings
Milos Raonic
CAN Age 35 Right-Handed 196 cm / 6'5"

H2H Match Log

PlayerScorePlayerMatch DataDateRoundTournamentCategorySurface
Grigor Dimitrov #20 (w/o) Milos Raonic #19 Match data Oct 24, 2020* QF Antwerp ATP 250 Hard
Milos Raonic #24 7-5 3-6 6-3 Grigor Dimitrov #4 Match data May 9, 2018* R32 Madrid Open Masters 1000 Clay
Grigor Dimitrov #17 7-6(7) 6-2 Milos Raonic #3 Match data Jan 7, 2017* SF Brisbane International ATP 250 Hard
Grigor Dimitrov #20 (w/o) Milos Raonic #6 Match data Oct 8, 2016* SF China Open ATP 500 Hard
Grigor Dimitrov #22 6-3 3-6 6-4 7-6(10) Milos Raonic #11 Match data Jan 19, 2014* R32 Australian Open Grand Slam Hard
Grigor Dimitrov #48 6-3 6-4 Milos Raonic #13 Match data Jan 4, 2013* R16 Brisbane International ATP 250 Hard
Milos Raonic #29 7-5 6-4 Grigor Dimitrov #70 Match data Oct 22, 2011* QF Stockholm Open ATP 250 Hard

Estimated match date where the exact historical date is unavailable. Arrows show an edition's recorded category and documented modern equivalent; unresolved editions keep their recorded category. Asterisked totals include editions mapped from documented historical predecessor categories. Mapping details.

Career Comparison

Player Current Peak Pts Elo W L Win % GS 1000 including documented historical predecessor categories Finals 500 including documented historical predecessor categories 250 including documented historical predecessor categories Titles
Grigor Dimitrov #137 #3 5,150 2,170 477 314 60.3% 0 1 1 1 6 9
Milos Raonic #634 #3 5,450 2,248 370 188 66.3% 0 0 0 1 7 8

Career Progression by Age

Seasons are aligned by the age each player spent most of that calendar year. GS and Titles are cumulative career totals through that season.

Age Grigor Dimitrov Milos Raonic
YrW-LWin %RankEloGSTitles YrW-LWin %RankEloGSTitles
17 2008 0–1 0.0% #493 1,478 0 0 — — — — — — —
18 2009 2–6 25.0% #288 1,489 0 0 2009 0–1 0.0% #373 1,535 0 0
19 2010 1–1 50.0% #106 1,493 0 0 2010 3–4 42.9% #156 1,651 0 0
20 2011 18–25 41.9% #76 1,740 0 0 2011 30–18 62.5% #31 1,834 0 1
21 2012 24–19 55.8% #48 1,845 0 0 2012 43–21 67.2% #13 1,980 0 3
22 2013 35–23 60.3% #23 1,955 0 1 2013 41–21 66.1% #11 2,036 0 5
23 2014 50–18 73.5% #11 2,092 0 4 2014 47–20 70.1% #8 2,088 0 6
24 2015 32–22 59.3% #28 1,951 0 4 2015 32–15 68.1% #14 2,048 0 7
25 2016 40–26 60.6% #17 2,002 0 4 2016 52–19 73.2% #3 2,162 0 8
26 2017 49–19 72.1% #3 2,134 0 8 2017 29–14 67.4% #24 2,078 0 8
27 2018 24–19 55.8% #19 1,934 0 8 2018 31–18 63.3% #18 1,975 0 8
28 2019 23–21 52.3% #20 1,928 0 8 2019 23–13 63.9% #31 1,934 0 8
29 2020 17–10 63.0% #19 1,936 0 8 2020 23–10 69.7% #14 2,016 0 8
30 2021 24–18 57.1% #28 1,932 0 8 2021 6–4 60.0% #70 1,978 0 8
31 2022 26–22 54.2% #28 1,863 0 8 — — — — — — —
32 2023 41–21 66.1% #14 2,094 0 8 2023 4–4 50.0% #317 1,918 0 8
33 2024 45–18 71.4% #10 2,011 0 9 2024 6–6 50.0% #238 1,897 0 8
34 2025 18–12 60.0% #44 1,958 0 9 — — — — — — —
35 2026 8–13 38.1% #137 1,770 0 9 — — — — — — —

Surface Results by Age

Seasons are aligned by the age each player spent most of that calendar year. Results cover completed main-draw matches. Bold green marks the higher win percentage when both players have at least 5 matches on that surface at the aligned age.

Age Grigor Dimitrov Milos Raonic
Yr HardClayGrass Yr HardClayGrass
W L M Win % W L M Win % W L M Win % W L M Win % W L M Win % W L M Win %
17 2008 — — — — — — — — 0 1 1 0.0% — — — — — — — — — — — — —
18 2009 1 3 4 25.0% 0 1 1 0.0% 1 2 3 33.3% 2009 0 1 1 0.0% — — — — — — — —
19 2010 — — — — — — — — 1 1 2 50.0% 2010 3 4 7 42.9% — — — — — — — —
20 2011 11 16 27 40.7% 3 5 8 37.5% 4 4 8 50.0% 2011 20 10 30 66.7% 7 6 13 53.8% 3 2 5 60.0%
21 2012 10 11 21 47.6% 8 5 13 61.5% 6 3 9 66.7% 2012 31 12 43 72.1% 7 5 12 58.3% 5 4 9 55.6%
22 2013 22 15 37 59.5% 11 6 17 64.7% 2 2 4 50.0% 2013 33 13 46 71.7% 7 5 12 58.3% 1 3 4 25.0%
23 2014 28 13 41 68.3% 12 4 16 75.0% 10 1 11 90.9% 2014 31 13 44 70.5% 11 5 16 68.8% 5 2 7 71.4%
24 2015 20 15 35 57.1% 9 5 14 64.3% 3 2 5 60.0% 2015 24 11 35 68.6% 4 2 6 66.7% 4 2 6 66.7%
25 2016 34 18 52 65.4% 4 5 9 44.4% 2 3 5 40.0% 2016 32 13 45 71.1% 10 4 14 71.4% 10 2 12 83.3%
26 2017 39 11 50 78.0% 4 5 9 44.4% 6 3 9 66.7% 2017 14 7 21 66.7% 11 5 16 68.8% 4 2 6 66.7%
27 2018 16 12 28 57.1% 7 5 12 58.3% 1 2 3 33.3% 2018 18 13 31 58.1% 4 2 6 66.7% 9 3 12 75.0%
28 2019 18 13 31 58.1% 5 6 11 45.5% 0 2 2 0.0% 2019 15 10 25 60.0% — — — — 8 3 11 72.7%
29 2020 11 8 19 57.9% 6 2 8 75.0% — — — — 2020 22 9 31 71.0% 1 1 2 50.0% — — — —
30 2021 20 12 32 62.5% 3 5 8 37.5% 1 1 2 50.0% 2021 6 4 10 60.0% — — — — — — — —
31 2022 15 15 30 50.0% 10 5 15 66.7% 1 2 3 33.3% — — — — — — — — — — — — —
32 2023 26 13 39 66.7% 10 6 16 62.5% 5 2 7 71.4% 2023 2 2 4 50.0% — — — — 2 2 4 50.0%
33 2024 33 12 45 73.3% 8 4 12 66.7% 4 2 6 66.7% 2024 3 3 6 50.0% 0 1 1 0.0% 3 2 5 60.0%
34 2025 10 7 17 58.8% 5 4 9 55.6% 3 1 4 75.0% — — — — — — — — — — — — —
35 2026 2 8 10 20.0% 1 3 4 25.0% 5 2 7 71.4% — — — — — — — — — — — — —
Career — 316 202 518 61.0% 106 76 182 58.2% 55 36 91 60.4% — 254 125 379 67.0% 62 36 98 63.3% 54 27 81 66.7%

Performance Progression by Age

Seasons are aligned by the age each player spent most of that calendar year. Detailed serve and return statistics available for 781/791 of Grigor Dimitrov's and 537/558 of Milos Raonic's main draw matches. Sample is shown as matches with detailed serve and return statistics / total main draw matches. Bold green marks the stronger value when both stat samples contain at least 5 matches; lower is better for DFs/M.

Age Grigor Dimitrov Milos Raonic
Yr Sample Aces/M DFs/M 1st Sv% 1st Pts% 2nd Pts% BP Saved% BP Conv% Svc Pts% Ret Pts% Yr Sample Aces/M DFs/M 1st Sv% 1st Pts% 2nd Pts% BP Saved% BP Conv% Svc Pts% Ret Pts%
17 2008 1/1 1.0 3.0 70.8% 58.8% 35.7% 33.3% 0.0% 52.1% 20.9% — —/— — — — — — — — — —
18 2009 8/8 4.8 3.1 58.8% 69.4% 43.1% 46.4% 36.1% 58.5% 30.4% 2009 1/1 20.0 3.0 58.2% 85.9% 45.7% 85.7% 20.0% 69.1% 33.0%
19 2010 2/2 8.5 3.0 55.4% 75.2% 40.1% 53.6% 28.6% 59.3% 27.1% 2010 7/7 14.0 3.7 59.6% 79.1% 45.1% 63.7% 22.7% 65.7% 28.0%
20 2011 43/43 5.4 3.7 59.6% 70.9% 50.5% 55.6% 36.8% 62.6% 35.9% 2011 47/48 13.6 2.2 63.9% 78.9% 54.7% 66.3% 42.8% 70.1% 33.8%
21 2012 41/43 7.3 2.8 62.6% 72.6% 53.3% 65.4% 38.7% 65.5% 35.9% 2012 60/64 16.2 3.3 61.3% 82.6% 57.2% 70.4% 46.2% 73.2% 34.7%
22 2013 58/58 8.1 2.8 61.7% 77.0% 51.5% 58.3% 43.5% 67.2% 36.8% 2013 60/62 14.7 3.0 62.9% 82.8% 54.1% 66.2% 39.3% 72.2% 33.6%
23 2014 67/68 7.8 3.2 60.7% 77.6% 54.1% 59.6% 45.6% 68.4% 37.7% 2014 67/67 16.5 3.1 61.4% 82.6% 55.3% 66.1% 43.1% 72.0% 33.9%
24 2015 54/54 7.3 2.8 62.3% 75.8% 53.0% 63.2% 39.4% 67.3% 37.4% 2015 47/47 15.8 3.0 63.0% 81.5% 58.3% 75.5% 32.7% 73.0% 31.0%
25 2016 64/66 5.8 3.4 64.3% 73.3% 52.7% 59.2% 43.2% 65.9% 37.6% 2016 69/71 12.7 3.3 63.9% 80.9% 56.9% 69.0% 40.5% 72.2% 36.6%
26 2017 68/68 8.2 3.7 62.6% 79.1% 53.6% 66.2% 40.1% 69.3% 39.0% 2017 40/43 14.2 3.5 63.3% 80.4% 57.1% 65.3% 42.0% 71.8% 35.6%
27 2018 43/43 7.7 5.2 61.4% 73.6% 48.8% 59.5% 37.5% 64.2% 35.0% 2018 45/49 17.5 4.0 63.2% 83.4% 58.0% 57.4% 35.7% 74.2% 34.0%
28 2019 43/44 7.3 4.2 62.3% 74.9% 50.0% 59.9% 46.6% 65.5% 37.4% 2019 34/36 19.7 3.7 62.9% 84.7% 57.2% 63.3% 35.8% 74.5% 34.7%
29 2020 26/27 4.7 4.3 61.7% 72.4% 51.6% 66.4% 46.4% 64.0% 41.2% 2020 32/33 16.5 3.4 63.0% 84.0% 56.9% 78.8% 40.7% 74.0% 36.0%
30 2021 42/42 5.0 3.5 63.6% 74.4% 51.3% 61.6% 43.2% 65.9% 39.4% 2021 10/10 16.6 5.1 60.3% 80.5% 57.8% 64.1% 42.8% 71.4% 37.4%
31 2022 48/48 5.6 2.9 63.1% 76.0% 51.7% 55.2% 41.7% 67.0% 36.9% — —/— — — — — — — — — —
32 2023 60/62 7.3 3.4 61.1% 77.0% 50.7% 62.2% 43.9% 66.9% 38.6% 2023 8/8 17.8 6.1 60.8% 82.6% 46.8% 70.2% 37.0% 68.5% 29.8%
33 2024 63/63 8.4 3.7 61.3% 80.7% 53.7% 61.1% 40.2% 70.2% 37.7% 2024 10/12 16.7 3.2 62.3% 83.2% 57.4% 52.9% 23.8% 73.2% 32.5%
34 2025 29/30 7.5 3.4 59.4% 74.4% 50.7% 55.8% 36.9% 64.9% 36.4% — —/— — — — — — — — — —
35 2026 21/21 8.7 4.6 61.3% 74.5% 47.9% 45.2% 36.7% 64.1% 33.8% — —/— — — — — — — — — —
Career — 781/791 7.1 3.5 61.9% 75.7% 51.8% 60.1% 41.4% 66.5% 37.3% — 537/558 15.6 3.3 62.7% 82.0% 56.2% 67.4% 39.7% 72.4% 34.3%

Advanced Statistics Comparison by Age

Seasons are aligned by the age each player spent most of that calendar year. Metrics are precomputed from eligible main-draw results; point-stat values use the available detailed sample. Bold green marks the stronger value when both underlying samples are sufficient. Lower is better for Schedule because a negative value means a tougher schedule. Career Schedule is normalized per 100 matches.

Age Grigor Dimitrov Milos Raonic
Yr Elo P+ Serve+ Return+ PD TPW% Hard Elo Clay Elo Grass Elo Set Win % Set Margin Dec. Set Tiebreak Pressure+ Schedule Yr Elo P+ Serve+ Return+ PD TPW% Hard Elo Clay Elo Grass Elo Set Win % Set Margin Dec. Set Tiebreak Pressure+ Schedule
17 2008 1479 90.8 -1.82 +0.78 0.437 37.4% — — — 0.0% -4.00 — — — -0.09 2008 1488 99.3 — — — — — — — — — — — — —
18 2009 1490 121.9 -1.06 -2.37 0.732 45.0% +40 — +34 33.3% -0.89 2–2 (50%) 0–3 (0%) — -0.06 2009 1535 118.1 +0.53 +4.04 1.069 51.1% — — — 33.3% -0.33 0–1 0–1 — -0.13
19 2010 1493 103.4 -2.32 -0.55 0.667 44.5% — — — 40.0% -0.60 1–0 — — +0.02 2010 1652 123.4 +0.54 -3.37 0.816 47.5% +23 — — 42.1% -0.74 2–1 (67%) 3–1 (75%) — +0.22
20 2011 1740 144.9 -0.28 -0.43 0.959 49.3% +7 -209 -140 42.0% -0.20 6–5 (55%) 9–10 (47%) — -0.35 2011 1835 152.5 +5.93 -1.86 1.129 51.6% +62 -201 -204 61.2% +0.49 10–7 (59%) 22–12 (65%) — +0.34
21 2012 1845 146.9 +2.63 -0.68 1.039 50.7% -52 -102 -118 54.2% +0.23 8–4 (67%) 12–13 (48%) — -1.45 2012 1980 165.4 +9.03 -1.07 1.292 53.5% +43 -208 -253 65.4% +0.85 8–9 (47%) 27–22 (55%) — +1.28
22 2013 1955 168.1 +4.20 +0.76 1.120 51.9% -13 -58 -221 55.8% +0.52 11–7 (61%) 9–13 (41%) — -1.02 2013 2037 163.9 +7.91 -1.26 1.212 52.2% +56 -201 -372 62.5% +0.72 9–5 (64%) 19–17 (53%) — +1.75
23 2014 2093 169.3 +4.59 +2.51 1.192 52.9% -39 -97 -71 64.0% +0.90 18–4 (82%) 20–14 (59%) — -0.89 2014 2089 170.2 +7.97 -0.86 1.213 52.8% +12 -85 -241 66.9% +0.85 11–7 (61%) 38–13 (75%) — +3.89
24 2015 1951 164.5 +2.92 +1.96 1.144 52.0% +20 +74 +48 56.7% +0.38 11–10 (52%) 15–10 (60%) — +0.70 2015 2048 167.3 +7.76 -2.58 1.147 52.1% +48 -7 -157 62.1% +0.81 12–4 (75%) 22–19 (54%) — +1.09
25 2016 2002 165.1 +2.53 +2.13 1.103 51.5% +34 -107 -45 57.3% +0.34 13–12 (52%) 22–12 (65%) — +0.60 2016 2163 173.6 +8.50 +1.49 1.313 53.6% -7 -113 -8 69.4% +1.00 12–6 (67%) 27–14 (66%) — -1.03
26 2017 2135 173.4 +5.21 +3.48 1.271 53.8% +37 -256 -168 67.2% +1.06 14–12 (54%) 17–10 (63%) — -0.86 2017 2079 162.7 +6.78 +0.23 1.261 53.2% +49 -42 +25 66.7% +0.92 4–1 (80%) 16–11 (59%) — -0.68
27 2018 1935 162.0 +0.98 +0.10 0.977 49.9% +68 -30 +8 52.1% +0.11 11–8 (58%) 15–9 (63%) — -0.60 2018 1975 153.8 +8.35 -0.88 1.318 53.1% +7 +61 +177 64.0% +0.70 5–5 (50%) 18–11 (62%) — +1.79
28 2019 1929 159.5 +1.70 +2.11 1.083 51.2% +44 -27 — 51.7% +0.43 6–7 (46%) 9–21 (30%) — -0.32 2019 1934 154.2 +7.20 -0.04 1.360 53.8% +1 — +195 67.8% +0.93 3–6 (33%) 19–9 (68%) — +1.72
29 2020 1937 153.3 +1.01 +3.79 1.145 52.8% -6 -28 — 60.6% +0.73 4–7 (36%) 8–8 (50%) — +0.24 2020 2017 164.6 +7.82 +0.28 1.382 54.3% +17 — — 72.2% +1.32 2–5 (29%) 13–8 (62%) — +0.12
30 2021 1933 159.4 +2.32 +3.30 1.156 52.4% +43 -91 — 55.8% +0.52 7–3 (70%) 6–10 (38%) — -0.28 2021 1979 139.0 +4.52 +0.69 1.309 53.5% +19 — — 62.1% +0.96 0–2 2–4 (33%) — +0.31
31 2022 1864 154.9 +2.60 +1.06 1.118 51.5% +7 +84 -57 53.6% +0.38 8–5 (62%) 10–12 (45%) — +1.43 — — — — — — — — — — — — — — — —
32 2023 2095 166.4 +3.66 +3.67 1.165 52.5% -15 -108 -209 63.6% +0.87 12–4 (75%) 18–16 (53%) — -3.30 2023 1919 127.9 +2.47 -1.58 0.944 49.3% +65 — +186 45.5% -0.23 1–0 3–4 (43%) — -0.07
33 2024 2011 162.4 +5.31 +2.38 1.263 53.3% +29 -22 -64 68.7% +1.06 12–8 (60%) 22–10 (69%) — +1.17 2024 1898 124.3 +5.72 -1.03 1.214 51.5% +70 — +199 61.9% +0.71 2–1 (67%) 3–4 (43%) — -0.82
34 2025 1959 144.8 +0.59 +1.48 1.035 50.6% +68 -56 0 65.6% +0.61 5–1 (83%) 8–3 (73%) — +0.39 — — — — — — — — — — — — — — — —
35 2026 1771 127.1 -0.23 -0.93 0.942 49.0% +61 +41 +178 43.3% -0.28 3–5 (38%) 4–4 (50%) — +0.37 — — — — — — — — — — — — — — — —
Career — 2171 167.1 +2.86 +1.80 1.114 51.7% +17 -58 -71 57.8% +0.52 152–104 (59%) 204–178 (53%) 104.1 -0.55 — 2248 169.1 +7.54 -0.67 1.241 52.8% +29 -114 -17 64.8% +0.80 81–60 (57%) 232–150 (61%) 107.6 +1.81

Career Rivalries

Each player's five most-played main-draw opponents. The current matchup is highlighted when it appears in a player's top five.