| 28‑Aug‑2023 | US Open | Hard | R128 | 337 | 7 | (7)Stefanos Tsitsipas [GRE] d. Raonic | 6-2 6-3 6-4 | (ch) | 160 | 8 | 8 | 84 | 39 | 45 | 7 | 1:56 |
| 3‑Jul‑2023 | Wimbledon | Grass | R64 | 849 | 15 | (16)Tommy Paul [USA] d. Raonic | 6-4 7-6(4) 6-7(4) 6-4 | (ch) | 267 | 21 | 8 | 142 | 89 | 53 | 13 | 3:01 |
| 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 |
| 14‑Jan‑2019 | Australian Open | Hard | QF | 17 | 31 | (28)Lucas Pouille [FRA] d. (16)Raonic | 7-6(4) 6-3 6-7(2) 6-4 | (ch) | 271 | 25 | 6 | 149 | 87 | 62 | 14 | 3:02 |
| 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 | R16 | 7 | 11 | (6)Raonic d. (11)David Goffin [BEL] | 4-6 3-6 6-4 6-4 6-4 | | 278 | 22 | 6 | 139 | 92 | 47 | 12 | 3:02 |
| 23‑May‑2016 | Roland Garros | Clay | R16 | 9 | 55 | Albert Ramos [ESP] d. (8)Raonic | 6-2 6-4 6-4 | | 194 | 7 | 4 | 96 | 62 | 34 | 2 | 2:19 |
| 31‑Aug‑2015 | US Open | Hard | R32 | 10 | 19 | (18)Feliciano Lopez [ESP] d. (10)Raonic | 6-2 7-6(4) 6-3 | | 205 | 12 | 7 | 110 | 63 | 47 | 16 | |
| 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 |
| 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 | | | | | | | | | |
| 24‑Jun‑2013 | Wimbledon | Grass | R64 | 15 | 64 | Igor Sijsling [NED] d. (17)Raonic | 7-5 6-4 7-6(4) | | 203 | 22 | 4 | 109 | 74 | 35 | 17 | 2:09 |
| 27‑May‑2013 | Roland Garros | Clay | R32 | 16 | 25 | (23)Kevin Anderson [RSA] d. (14)Raonic | 7-5 7-6(4) 6-3 | | 228 | 16 | 1 | 131 | 75 | 56 | 8 | 2:24 |
| 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 |
