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Drafted:
| Date | Opponent | G | A | PTS |
|---|---|---|---|---|
| May 13 | @  | 0 | 0 | 0 |
| May 11 | vs | 0 | 0 | 0 |
| May 9 | vs | 0 | 0 | 0 |
| May 5 | @ | 0 | 0 | 0 |
| May 3 | @ | 0 | 0 | 0 |
Middleton impacted the rebuilding San Jose Sharks during his rookie season, working his way to the NHL after signing a three-year, entry-level contract Sept. 7, 2017 and playing the next two seasons for San Jose of the American Hockey League. He made his NHL debut against the Tampa Bay Lightning hours after he was called up Jan. 5, 2019 and scored his first NHL point, an assist, in a 3-2 win at the Edmonton Oilers on April 4.
Selected by the Los Angeles Kings in the seventh round (No. 210) of the 2014 NHL Draft, Middleton began his playing career after he was chosen by Owen Sound in the 2012 Ontario Hockey League Draft, playing 14 games until he was traded to Ottawa on Jan. 7, 2013. He played five seasons in the AHL before becoming a regular with the Sharks in 2021-22, scoring his first NHL goal in a 6-3 win against the Ottawa Senators on Nov. 24, 2021.
He was traded to the Minnesota Wild for goalie Kaapo Kahkonen on March 21, 2022, and sent to the Calgary Flames by Minnesota on July 2, 2026.
No contract data available.
Traded to Calgary by Minnesota for Blake Coleman and Olli Maatta.
Traded to Calgary by Minnesota for Blake Coleman and Olli Maatta.
Traded to Minnesota by San Jose for Kaapo Kahkonen and a 5th-round pick in the 2022 NHL Draft.
Traded to Minnesota by San Jose for Kaapo Kahkonen and a 5th-round pick in the 2022 NHL Draft.
Signed as a free agent by San Jose.
Signed as a free agent by San Jose.
Signed as a free agent by San Jose (AHL).
Signed as a free agent by San Jose (AHL).
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