Khris Middleton averaged 16.1 points, 5.5 rebounds and 3.9 assists in 16 games against the Raptors between the 2019-20 and 2024-25 seasons.
| NAME | DATE | TM | OPP | MIN | PTS | REB | AST | STL | BLK | FGM | FGA | FG% | 3PM | 3PA | 3P% | FTM | FTA | FT% | TS% | OREB | DREB | TOV | PF | +/- | |||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 |  | K. Middleton | 11/2/2019 |  MIL | vs |  TOR | 34 | 11 | 4 | 7 | 0 | 0 | 4 | 12 | 33.3 | 0 | 4 | 0.0 | 3 | 4 | 75.0 | 40.0 | 1 | 3 | 3 | 3 | +4 |
| 2 | | K. Middleton | 2/25/2020 | MIL | @ | TOR | 32 | 22 | 8 | 3 | 0 | 0 | 7 | 14 | 50.0 | 2 | 4 | 50.0 | 6 | 7 | 85.7 | 64.4 | 0 | 8 | 2 | 4 | +6 |
| 3 | | K. Middleton | 8/10/2020 | MIL | vs | TOR | 25 | 17 | 4 | 3 | 0 | 0 | 6 | 12 | 50.0 | 0 | 2 | 0.0 | 5 | 5 | 100.0 | 59.9 | 0 | 4 | 4 | 4 | -11 |
| 4 | | K. Middleton | 1/27/2021 | MIL | @ | TOR | 35 | 24 | 10 | 7 | 1 | 0 | 8 | 17 | 47.1 | 5 | 8 | 62.5 | 3 | 3 | 100.0 | 65.5 | 1 | 9 | 1 | 3 | +2 |
| 5 | | K. Middleton | 2/16/2021 | MIL | vs | TOR | 38 | 11 | 7 | 0 | 2 | 0 | 4 | 8 | 50.0 | 1 | 3 | 33.3 | 2 | 2 | 100.0 | 61.9 | 0 | 7 | 5 | 4 | -19 |
| 6 | | K. Middleton | 2/18/2021 | MIL | vs | TOR | 37 | 13 | 8 | 5 | 1 | 0 | 5 | 13 | 38.5 | 0 | 3 | 0.0 | 3 | 3 | 100.0 | 45.4 | 2 | 6 | 6 | 4 | -16 |
| 7 | | K. Middleton | 12/2/2021 | MIL | @ | TOR | 35 | 22 | 8 | 2 | 0 | 1 | 8 | 20 | 40.0 | 2 | 5 | 40.0 | 4 | 5 | 80.0 | 49.5 | 1 | 7 | 3 | 1 | +2 |
| 8 | | K. Middleton | 1/5/2022 | MIL | vs | TOR | 34 | 25 | 6 | 4 | 1 | 2 | 9 | 16 | 56.3 | 1 | 3 | 33.3 | 6 | 8 | 75.0 | 64.0 | 2 | 4 | 4 | 4 | -8 |
| 9 | | K. Middleton | 1/15/2022 | MIL | vs | TOR | 37 | 16 | 4 | 5 | 3 | 2 | 3 | 12 | 25.0 | 2 | 6 | 33.3 | 8 | 9 | 88.9 | 50.1 | 0 | 4 | 3 | 1 | +1 |
| 10 | | K. Middleton | 3/19/2023 | MIL | vs | TOR | 32 | 20 | 8 | 5 | 0 | 1 | 7 | 13 | 53.8 | 5 | 8 | 62.5 | 1 | 2 | 50.0 | 72.0 | 2 | 6 | 4 | 3 | +2 |
| 11 | | K. Middleton | 11/1/2023 | MIL | @ | TOR | 17 | 11 | 3 | 0 | 1 | 0 | 4 | 10 | 40.0 | 1 | 4 | 25.0 | 2 | 2 | 100.0 | 50.6 | 0 | 3 | 4 | 2 | -13 |
| 12 | | K. Middleton | 11/15/2023 | MIL | @ | TOR | 20 | 11 | 5 | 4 | 2 | 0 | 5 | 9 | 55.6 | 1 | 2 | 50.0 | 0 | 0 | 61.1 | 1 | 4 | 4 | 3 | +12 | |
| 13 | | K. Middleton | 4/5/2024 | MIL | vs | TOR | 34 | 21 | 5 | 6 | 3 | 0 | 9 | 16 | 56.3 | 2 | 6 | 33.3 | 1 | 2 | 50.0 | 62.2 | 1 | 4 | 2 | 5 | -11 |
| 14 | | K. Middleton | 1/17/2025 | MIL | vs | TOR | 24 | 13 | 3 | 5 | 1 | 1 | 4 | 6 | 66.7 | 2 | 3 | 66.7 | 3 | 3 | 100.0 | 88.8 | 1 | 2 | 0 | 2 | +9 |
| 15 |  | K. Middleton | 3/8/2025 |  WAS | @ | TOR | 24 | 12 | 3 | 2 | 2 | 0 | 4 | 9 | 44.4 | 1 | 5 | 20.0 | 3 | 4 | 75.0 | 55.8 | 1 | 2 | 2 | 1 | +7 |
| 16 | | K. Middleton | 3/24/2025 | WAS | vs | TOR | 22 | 9 | 2 | 5 | 1 | 0 | 2 | 7 | 28.6 | 0 | 2 | 0.0 | 5 | 5 | 100.0 | 48.9 | 0 | 2 | 1 | 2 | +8 |
| Average | 29.9 | 16.1 | 5.5 | 3.9 | 1.1 | 0.4 | 5.6 | 12.1 | 45.9 | 1.6 | 4.3 | 36.8 | 3.4 | 4.0 | 85.9 | 58.1 | 0.8 | 4.7 | 3.0 | 2.9 | -1.6 | ||||||
| Total | 479 | 258 | 88 | 63 | 18 | 7 | 89 | 194 | 45.9 | 25 | 68 | 36.8 | 55 | 64 | 85.9 | 58.1 | 13 | 75 | 48 | 46 | -25 |
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