| 10‑Jun‑2019 | Stuttgart | Grass | SF | 18 | 21 | (7)Felix Auger Aliassime [CAN] d. (6)Raonic | W/O | | | | | | | | | |
| 10‑Jun‑2019 | Stuttgart | Grass | QF | 18 | 52 | (6)Raonic d. Marton Fucsovics [HUN] | 6-4 6-4 | | 1.93 | 22.6% | 7.5% | 67.9% | 88.9% | 58.8% | 1/1 | 1:13 |
| 10‑Jun‑2019 | Stuttgart | Grass | R16 | 18 | 79 | (6)Raonic d. (PR)Jo Wilfried Tsonga [FRA] | 6-4 6-7(5) 7-6(1) | | 0.89 | 21.4% | 7.1% | 58.0% | 83.1% | 57.4% | 4/4 | 2:27 |
| 10‑Jun‑2019 | Stuttgart | Grass | R32 | 18 | 103 | (6)Raonic d. (Q)Alexei Popyrin [AUS] | 6-7(6) 6-4 7-6(4) | | 1.26 | 30.4% | 4.9% | 49.0% | 94.0% | 63.5% | 1/2 | 2:12 |
| 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 |
| 11‑Jun‑2018 | Stuttgart | Grass | SF | 35 | 17 | (7)Raonic d. (2)Lucas Pouille [FRA] | 6-4 7-6(3) | | 1.66 | 29.2% | 3.1% | 56.9% | 86.5% | 75.0% | 1/1 | 1:34 |
| 11‑Jun‑2018 | Stuttgart | Grass | QF | 35 | 19 | (7)Raonic d. (3)Tomas Berdych [CZE] | 7-6(2) 7-6(1) | | 1.00 | 31.2% | 3.9% | 72.7% | 80.4% | 66.7% | 2/2 | 1:32 |
| 11‑Jun‑2018 | Stuttgart | Grass | R16 | 35 | 46 | (7)Raonic d. Marton Fucsovics [HUN] | 6-2 6-4 | | 2.46 | 44.2% | 4.7% | 65.1% | 85.7% | 80.0% | 0/0 | 0:51 |
| 11‑Jun‑2018 | Stuttgart | Grass | R32 | 35 | 78 | (7)Raonic d. Mirza Basic [BIH] | 7-6(8) 6-2 | | 2.19 | 25.9% | 6.9% | 62.1% | 97.2% | 59.1% | 0/0 | 1:23 |
