| 8‑Feb‑2021 | Australian Open | Hard | R16 | 14 | 1 | (1)Novak Djokovic [SRB] d. (14)Raonic | 7-6(4) 4-6 6-1 6-4 | (ch) | 0.80 | 21.1% | 2.4% | 61.0% | 76.0% | 47.9% | 8/11 | 2:56 |
| 24‑Aug‑2020 | Cincinnati Masters | Hard | F | 30 | 1 | (1)Novak Djokovic [SRB] d. Raonic | 1-6 6-3 6-4 | (ch) | 1.04 | 14.1% | 4.2% | 64.8% | 76.1% | 40.0% | 2/5 | 2:00 |
| 24‑Aug‑2020 | Cincinnati Masters | Hard | R16 | 30 | 134 | Raonic d. (WC)Andy Murray [GBR] | 6-2 6-2 | | 1.75 | 21.3% | 4.3% | 53.2% | 88.0% | 54.5% | 2/2 | 1:28 |
| 20‑Jan‑2020 | Australian Open | Hard | QF | 35 | 2 | (2)Novak Djokovic [SRB] d. (32)Raonic | 6-4 6-3 7-6(1) | (ch) | 0.66 | 14.1% | 4.7% | 63.3% | 71.6% | 42.6% | 14/16 | 2:49 |
| 20‑Sep‑2019 | Laver Cup | Hard | RR | 24 | 2 | Rafael Nadal [ESP] d. Raonic | 6-3 7-6(1) | (ch) | | | | | | | | |
| 29‑Oct‑2018 | Paris Masters | Hard | R32 | 21 | 3 | (3)Roger Federer [SUI] d. Raonic | W/O | | | | | | | | | |
| 13‑Aug‑2018 | Cincinnati Masters | Hard | QF | 29 | 10 | (10)Novak Djokovic [SRB] d. Raonic | 7-5 4-6 6-3 | | 0.88 | 19.3% | 8.3% | 58.7% | 76.6% | 40.0% | 10/14 | 2:31 |
| 11‑Jun‑2018 | Stuttgart | Grass | F | 35 | 2 | (1)Roger Federer [SUI] d. (7)Raonic | 6-4 7-6(3) | (ch) | 0.82 | 23.0% | 4.9% | 72.1% | 77.3% | 58.8% | 0/1 | 1:18 |
| 3‑Jul‑2017 | Wimbledon | Grass | QF | 7 | 5 | (3)Roger Federer [SUI] d. (6)Raonic | 6-4 6-2 7-6(4) | (ch) | 0.59 | 11.5% | 0.0% | 72.9% | 71.4% | 42.3% | 3/6 | 1:57 |
| 16‑Jan‑2017 | Australian Open | Hard | QF | 3 | 9 | (9)Rafael Nadal [ESP] d. (3)Raonic | 6-4 7-6(7) 6-4 | (ch) | 0.71 | 13.1% | 1.9% | 66.4% | 67.6% | 55.6% | 1/3 | 2:44 |
| 2‑Jan‑2017 | Brisbane | Hard | QF | 3 | 9 | (1)Raonic d. (5)Rafael Nadal [ESP] | 4-6 6-3 6-4 | | 1.15 | 23.7% | 3.1% | 63.9% | 80.6% | 45.7% | 6/7 | 2:20 |
| 14‑Nov‑2016 | Tour Finals | Hard | SF | 4 | 1 | (1)Andy Murray [GBR] d. (4)Raonic | 5-7 7-6(5) 7-6(9) | (ch) | 1.03 | 7.8% | 4.7% | 63.3% | 74.1% | 44.7% | 4/7 | 3:38 |
| 14‑Nov‑2016 | Tour Finals | Hard | RR | 4 | 2 | (2)Novak Djokovic [SRB] d. (4)Raonic | 7-6(6) 7-6(5) | (ch) | 1.02 | 17.9% | 3.8% | 57.7% | 84.4% | 36.4% | 0/2 | 2:14 |
| 31‑Oct‑2016 | Paris Masters | Hard | SF | 5 | 2 | (2)Andy Murray [GBR] d. (4)Raonic | W/O | | | | | | | | | |
| 15‑Aug‑2016 | Cincinnati Masters | Hard | SF | 6 | 2 | (1)Andy Murray [GBR] d. (4)Raonic | 6-3 6-3 | (ch) | 0.72 | 16.7% | 10.4% | 60.4% | 82.8% | 26.3% | 1/4 | 1:30 |
| 27‑Jun‑2016 | Wimbledon | Grass | F | 7 | 2 | (2)Andy Murray [GBR] d. (6)Raonic | 6-4 7-6(3) 7-6(2) | (ch) | 0.74 | 7.0% | 0.9% | 64.0% | 67.1% | 70.7% | 6/7 | 2:48 |
| 27‑Jun‑2016 | Wimbledon | Grass | SF | 7 | 3 | (6)Raonic d. (3)Roger Federer [SUI] | 6-3 6-7(3) 4-6 7-5 6-3 | (ch) | 1.04 | 13.8% | 6.6% | 67.7% | 83.2% | 46.3% | 8/9 | 3:24 |
| 13‑Jun‑2016 | Queen's Club | Grass | F | 9 | 2 | (1)Andy Murray [GBR] d. (3)Raonic | 6-7(5) 6-4 6-3 | (ch) | 0.84 | 15.1% | 3.2% | 73.1% | 77.9% | 44.0% | 3/7 | 2:13 |
| 2‑May‑2016 | Madrid Masters | Clay | QF | 10 | 1 | (1)Novak Djokovic [SRB] d. (11)Raonic | 6-3 6-4 | (ch) | 0.69 | 5.8% | 2.9% | 68.1% | 66.0% | 45.5% | 8/10 | 1:44 |
| 11‑Apr‑2016 | Monte Carlo Masters | Clay | QF | 12 | 2 | (2)Andy Murray [GBR] d. (10)Raonic | 6-2 6-0 | | 0.42 | 0.0% | 0.0% | 48.9% | 52.2% | 37.5% | 4/9 | 1:06 |
| 7‑Mar‑2016 | Indian Wells Masters | Hard | F | 14 | 1 | (1)Novak Djokovic [SRB] d. (12)Raonic | 6-2 6-0 | (ch) | 0.47 | 6.7% | 3.3% | 50.0% | 76.7% | 10.0% | 6/11 | 1:17 |
| 18‑Jan‑2016 | Australian Open | Hard | SF | 14 | 2 | (2)Andy Murray [GBR] d. (13)Raonic | 4-6 7-5 6-7 6-4 6-2 | (ch) | 0.72 | 13.4% | 4.7% | 66.9% | 76.5% | 43.9% | 12/16 | 4:03 |
| 4‑Jan‑2016 | Brisbane | Hard | F | 14 | 3 | (4)Raonic d. (1)Roger Federer [SUI] | 6-4 6-4 | (ch) | 1.20 | 10.0% | 10.0% | 56.7% | 82.4% | 53.8% | 1/1 | 1:27 |
| 11‑Oct‑2015 | Shanghai Masters | Hard | R16 | 9 | 7 | (8)Rafael Nadal [ESP] d. (9)Raonic | 6-3 7-6(3) | | 0.71 | 13.2% | 2.9% | 58.8% | 77.5% | 53.6% | 4/5 | |
| 3‑May‑2015 | Madrid Masters | Clay | QF | 6 | 3 | (2)Andy Murray [GBR] d. (5)Raonic | 6-4 7-5 | | 0.80 | 12.1% | 6.1% | 59.1% | 82.1% | 40.7% | 4/6 | 1:41 |
| 12‑Mar‑2015 | Indian Wells Masters | Hard | SF | 6 | 2 | (2)Roger Federer [SUI] d. (6)Raonic | 7-5 6-4 | (ch) | 0.81 | 14.1% | 1.6% | 57.8% | 75.7% | 59.3% | 5/7 | 1:26 |
| 12‑Mar‑2015 | Indian Wells Masters | Hard | QF | 6 | 3 | (6)Raonic d. (3)Rafael Nadal [ESP] | 4-6 7-6(10) 7-5 | (ch) | 0.76 | 16.0% | 5.0% | 61.3% | 80.8% | 47.8% | 6/7 | 2:58 |
| 19‑Jan‑2015 | Australian Open | Hard | QF | 8 | 1 | (1)Novak Djokovic [SRB] d. (8)Raonic | 7-6(5) 6-4 6-2 | (ch) | 0.45 | 17.2% | 2.0% | 67.7% | 71.6% | 53.1% | 8/11 | 2:00 |
| 4‑Jan‑2015 | Brisbane | Hard | F | 8 | 2 | (1)Roger Federer [SUI] d. (3)Raonic | 6-4 6-7(2) 6-4 | (ch) | 0.88 | 13.0% | 3.7% | 53.7% | 75.9% | 54.0% | 4/7 | 2:13 |
| 9‑Nov‑2014 | Tour Finals | Hard | RR | 8 | 2 | (2)Roger Federer [SUI] d. (8)Raonic | 6-1 7-6(0) | (ch) | 0.80 | 16.7% | 3.3% | 46.7% | 78.6% | 46.9% | 4/6 | 1:29 |
| 9‑Nov‑2014 | Tour Finals | Hard | RR | 8 | 6 | (5)Andy Murray [GBR] d. (8)Raonic | 6-3 7-5 | (ch) | 0.83 | 6.5% | 3.2% | 53.2% | 69.7% | 48.3% | 2/5 | 1:32 |
| 27‑Oct‑2014 | Paris Masters | Hard | F | 10 | 1 | (1)Novak Djokovic [SRB] d. (7)Raonic | 6-2 6-3 | (ch) | 0.60 | 16.1% | 3.6% | 66.1% | 64.9% | 36.8% | 6/9 | 1:23 |
| 27‑Oct‑2014 | Paris Masters | Hard | QF | 10 | 2 | (7)Raonic d. (2)Roger Federer [SUI] | 7-6(5) 7-5 | (ch) | 1.15 | 30.0% | 1.4% | 67.1% | 85.1% | 65.2% | 1/1 | 1:33 |
| 10‑Aug‑2014 | Cincinnati Masters | Hard | SF | 7 | 3 | (2)Roger Federer [SUI] d. (5)Raonic | 6-2 6-3 | (ch) | 0.59 | 10.5% | 5.3% | 43.9% | 68.0% | 50.0% | 2/5 | 1:09 |
| 23‑Jun‑2014 | Wimbledon | Grass | SF | 9 | 4 | (4)Roger Federer [SUI] d. (8)Raonic | 6-4 6-4 6-4 | (ch) | 0.71 | 20.2% | 4.8% | 54.8% | 80.4% | 50.0% | 4/7 | 1:41 |
| 26‑May‑2014 | Roland Garros | Clay | QF | 9 | 2 | (2)Novak Djokovic [SRB] d. (8)Raonic | 7-5 7-6(5) 6-4 | | 0.71 | 18.4% | 3.5% | 70.2% | 78.8% | 29.4% | 6/9 | 2:22 |
| 11‑May‑2014 | Rome Masters | Clay | SF | 10 | 2 | (2)Novak Djokovic [SRB] d. (8)Raonic | 6-7(5) 7-6(4) 6-3 | (ch) | 0.88 | 14.0% | 2.5% | 66.9% | 75.3% | 45.0% | 7/10 | 3:01 |
| 19‑Mar‑2014 | Miami Masters | Hard | QF | 12 | 1 | (1)Rafael Nadal [ESP] d. (12)Raonic | 4-6 6-2 6-4 | (ch) | 0.73 | 7.8% | 4.9% | 55.3% | 75.4% | 39.1% | 6/9 | 2:36 |
| 6‑Mar‑2014 | Indian Wells Masters | Hard | R16 | 11 | 6 | (10)Raonic d. (5)Andy Murray [GBR] | 4-6 7-5 6-3 | (ch) | 1.37 | 18.8% | 3.8% | 66.3% | 83.0% | 51.9% | 0/2 | 2:10 |
| 13‑Sep‑2013 | Davis Cup WG SF: SRB vs CAN | Clay | RR | 11 | 1 | Novak Djokovic [SRB] d. Raonic | 7-6(1) 6-2 6-2 | | | | | | | | | |
| 5‑Aug‑2013 | Canada Masters | Hard | F | 13 | 4 | (4)Rafael Nadal [ESP] d. (11)Raonic | 6-2 6-2 | (ch) | 0.37 | 8.7% | 6.5% | 50.0% | 60.9% | 43.5% | 0/4 | 1:08 |
| 22‑Apr‑2013 | Barcelona | Clay | SF | 13 | 5 | (2)Rafael Nadal [ESP] d. (5)Raonic | 6-4 6-0 | | 0.59 | 10.5% | 0.0% | 66.7% | 57.9% | 26.3% | 6/11 | 1:12 |
| 14‑Jan‑2013 | Australian Open | Hard | R16 | 15 | 2 | (2)Roger Federer [SUI] d. (13)Raonic | 6-4 7-6(4) 6-2 | (ch) | 0.42 | 19.8% | 5.2% | 65.6% | 69.8% | 51.5% | 4/7 | 1:53 |
| 1‑Oct‑2012 | Tokyo | Hard | SF | 15 | 3 | (6)Raonic d. (1)Andy Murray [GBR] | 6-3 6-7(5) 7-6(4) | | 1.09 | 11.7% | 6.3% | 64.9% | 81.9% | 46.2% | 5/6 | 2:46 |
| 27‑Aug‑2012 | US Open | Hard | R16 | 16 | 4 | (3)Andy Murray [GBR] d. (15)Raonic | 6-4 6-4 6-2 | (ch) | 0.55 | 16.1% | 6.9% | 70.1% | 70.5% | 30.8% | 8/12 | 2:00 |
| 6‑Aug‑2012 | Canada Masters | Hard | R16 | 24 | 4 | (16)Raonic d. (2)Andy Murray [GBR] | W/O | | | | | | | | | |
| 11‑Jun‑2012 | Halle | Grass | QF | 21 | 3 | (2)Roger Federer [SUI] d. (5)Raonic | 6-7(4) 6-4 7-6(3) | | 0.78 | 25.3% | 2.0% | 65.7% | 89.2% | 52.9% | 3/4 | 1:59 |
| 6‑May‑2012 | Madrid Masters | Clay | R32 | 23 | 3 | (3)Roger Federer [SUI] d. Raonic | 4-6 7-5 7-6(4) | | 1.27 | 23.1% | 1.1% | 62.6% | 86.0% | 58.8% | 1/2 | 2:14 |
| 23‑Apr‑2012 | Barcelona | Clay | QF | 25 | 4 | (11)Raonic d. (2)Andy Murray [GBR] | 6-4 7-6(3) | | 1.35 | 20.3% | 1.4% | 65.2% | 84.4% | 54.2% | 3/4 | 1:44 |
| 21‑Mar‑2012 | Miami Masters | Hard | R32 | 26 | 4 | (4)Andy Murray [GBR] d. (26)Raonic | W/O | | | | | | | | | |
| 8‑Mar‑2012 | Indian Wells Masters | Hard | R32 | 27 | 3 | (3)Roger Federer [SUI] d. (27)Raonic | 6-7(4) 6-2 6-4 | | 0.70 | 10.4% | 6.3% | 56.3% | 75.9% | 57.1% | 1/4 | 2:08 |
| 3‑Oct‑2011 | Tokyo | Hard | R16 | 30 | 2 | (1)Rafael Nadal [ESP] d. Raonic | 7-5 6-3 | | 0.65 | 16.0% | 2.0% | 56.0% | 85.7% | 50.0% | 0/2 | 1:31 |
| 4‑Oct‑2010 | Tokyo | Hard | R16 | 200 | 1 | (1)Rafael Nadal [ESP] d. (Q)Raonic | 6-4 6-4 | | 0.74 | 26.9% | 1.9% | 67.3% | 85.7% | 29.4% | 0/2 | 1:13 |
