H2H data updated: 2026-07-18 07:16 UTC
Simone Bolelli vs Milos Raonic H2H: 1-3
Milos Raonic holds a 3–1 lead over Simone Bolelli in their ATP head-to-head. Across 4 main-draw meetings, Milos Raonic leads 2–1 on hard courts and 1–0 on clay. Most recently, Milos Raonic won the 2015 Indian Wells Masters second round 6-3 6-4.
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ITA
Age 40
Right-Handed
183 cm / 6'0"
H2H
1
–
3
4 main draw meetings
CAN
Age 35
Right-Handed
196 cm / 6'5"
H2H Match Log
| Date | Tournament | Category | Round | Surface | Winner | Score | Loser | Match |
|---|---|---|---|---|---|---|---|---|
| Mar 15, 2015* | Indian Wells Masters | Masters 1000 | R64 | Hard | Milos Raonic | 6-3 6-4 | Simone Bolelli | Match data |
| Feb 20, 2015* | Marseille | ATP 250 | R16 | Hard | Simone Bolelli | 6-4 3-6 7-6(3) | Milos Raonic | Match data |
| Feb 13, 2015* | Rotterdam | ATP 500 | R16 | Hard | Milos Raonic | 6-3 7-6(2) | Simone Bolelli | Match data |
| May 14, 2014* | Rome Masters | Masters 1000 | R32 | Clay | Milos Raonic | 6-3 7-6(5) | Simone Bolelli | Match data |
* Estimated match date where the exact historical date is unavailable.
Career Comparison
| Player | Current | Peak | Pts | Elo | W | L | Win % | GS | 1000 | Finals | 500 | 250 | Titles |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Simone Bolelli | #1,391 | #36 | 1,686 | 1,920 | 114 | 156 | 42.2% | 0 | 0 | 0 | 0 | 0 | 0 |
| Milos Raonic | #634 | #3 | 5,450 | 2,246 | 369 | 186 | 66.5% | 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 | Simone Bolelli | Milos Raonic | ||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Yr | W-L | Win % | Rank | Elo | GS | Titles | Yr | W-L | Win % | Rank | Elo | GS | Titles | |
| 18 | — | — | — | — | — | — | — | 2009 | 0–1 | 0.0% | #373 | 1,535 | 0 | 0 |
| 19 | — | — | — | — | — | — | — | 2010 | 3–4 | 42.9% | #156 | 1,651 | 0 | 0 |
| 20 | 2006 | 0–4 | 0.0% | #127 | 1,465 | 0 | 0 | 2011 | 30–18 | 62.5% | #31 | 1,839 | 0 | 1 |
| 21 | 2007 | 8–14 | 36.4% | #67 | 1,602 | 0 | 0 | 2012 | 42–20 | 67.7% | #13 | 1,987 | 0 | 3 |
| 22 | 2008 | 26–27 | 49.1% | #41 | 1,785 | 0 | 0 | 2013 | 41–21 | 66.1% | #11 | 2,034 | 0 | 5 |
| 23 | 2009 | 14–22 | 38.9% | #93 | 1,694 | 0 | 0 | 2014 | 47–20 | 70.1% | #8 | 2,087 | 0 | 6 |
| 24 | 2010 | 5–11 | 31.2% | #107 | 1,675 | 0 | 0 | 2015 | 32–15 | 68.1% | #14 | 2,047 | 0 | 7 |
| 25 | 2011 | 4–8 | 33.3% | #134 | 1,679 | 0 | 0 | 2016 | 52–19 | 73.2% | #3 | 2,143 | 0 | 8 |
| 26 | 2012 | 6–10 | 37.5% | #84 | 1,713 | 0 | 0 | 2017 | 29–14 | 67.4% | #24 | 2,053 | 0 | 8 |
| 27 | 2013 | 6–8 | 42.9% | #245 | 1,693 | 0 | 0 | 2018 | 31–18 | 63.3% | #18 | 1,952 | 0 | 8 |
| 28 | 2014 | 6–8 | 42.9% | #55 | 1,743 | 0 | 0 | 2019 | 23–13 | 63.9% | #31 | 1,919 | 0 | 8 |
| 29 | 2015 | 28–25 | 52.8% | #58 | 1,865 | 0 | 0 | 2020 | 23–10 | 69.7% | #14 | 1,996 | 0 | 8 |
| 30 | 2016 | 2–8 | 20.0% | #464 | 1,770 | 0 | 0 | 2021 | 6–4 | 60.0% | #70 | 1,964 | 0 | 8 |
| 31 | 2017 | 2–4 | 33.3% | #171 | 1,792 | 0 | 0 | — | — | — | — | — | — | — |
| 32 | 2018 | 5–4 | 55.6% | #141 | 1,783 | 0 | 0 | 2023 | 4–4 | 50.0% | #317 | 1,909 | 0 | 8 |
| 33 | 2019 | 1–3 | 25.0% | #334 | 1,734 | 0 | 0 | 2024 | 6–5 | 54.5% | #238 | 1,903 | 0 | 8 |
| 39 | 2025 | 1–0 | 100.0% | — | 1,741 | 0 | 0 | — | — | — | — | — | — | — |