| 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) | 244 | 26 | 3 | 123 | 75 | 48 | 10 | 2:56 |
| 20‑Jan‑2020 | Australian Open | Hard | QF | 35 | 2 | (2)Novak Djokovic [SRB] d. (32)Raonic | 6-4 6-3 7-6(1) | (ch) | 229 | 18 | 6 | 128 | 81 | 47 | 4 | 2:49 |
| 3‑Jul‑2017 | Wimbledon | Grass | QF | 7 | 5 | (3)Roger Federer [SUI] d. (6)Raonic | 6-4 6-2 7-6(4) | (ch) | 185 | 11 | 0 | 96 | 70 | 26 | 11 | 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) | 212 | 14 | 2 | 107 | 71 | 36 | 4 | 2:44 |
| 27‑Jun‑2016 | Wimbledon | Grass | F | 7 | 2 | (2)Andy Murray [GBR] d. (6)Raonic | 6-4 7-6(3) 7-6(2) | (ch) | 217 | 8 | 1 | 114 | 73 | 41 | 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) | 327 | 23 | 11 | 167 | 113 | 54 | 16 | 3:24 |
| 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) | 318 | 23 | 8 | 172 | 115 | 57 | 9 | 4:03 |
| 19‑Jan‑2015 | Australian Open | Hard | QF | 8 | 1 | (1)Novak Djokovic [SRB] d. (8)Raonic | 7-6(5) 6-4 6-2 | (ch) | 177 | 17 | 2 | 99 | 67 | 32 | 8 | 2:00 |
| 23‑Jun‑2014 | Wimbledon | Grass | SF | 9 | 4 | (4)Roger Federer [SUI] d. (8)Raonic | 6-4 6-4 6-4 | (ch) | 164 | 17 | 4 | 84 | 46 | 38 | 6 | 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 | | 212 | 21 | 4 | 114 | 80 | 34 | 4 | 2:22 |
| 14‑Jan‑2013 | Australian Open | Hard | R16 | 15 | 2 | (2)Roger Federer [SUI] d. (13)Raonic | 6-4 7-6(4) 6-2 | (ch) | 174 | 19 | 5 | 96 | 63 | 33 | 14 | 1:53 |
| 27‑Aug‑2012 | US Open | Hard | R16 | 16 | 4 | (3)Andy Murray [GBR] d. (15)Raonic | 6-4 6-4 6-2 | (ch) | 162 | 14 | 6 | 87 | 61 | 26 | 9 | 2:00 |
