Search Results
| Date | Team | Acquired | Relinquished | Notes |
| 2019-06-05 | Canadiens | • Antti Niemi | signed with Jokerit Helsinki (KHL-Russia) | |
| 2019-06-14 | Canadiens | • Gustav Olofsson | re-signed to a 1-year, $700K two way contract extension | |
| 2019-06-21 | Canadiens | • Cole Caufield | 2019 NHL entry draft first round pick (#15 overall) | |
| 2019-06-22 | Canadiens | • 2019 seventh round pick (#201-Rafael Harvey-Pinard) | • 2020 seventh round pick (#201-Gunnarwolfe Fontaine) | trade with Flyers |
| 2019-06-22 | Canadiens | • 2019 third round pick (#64-Mattias Norlinder) • 2019 fifth round pick (#126-Jacob Leguerrier) |
• 2019 second round pick (#50-Samuel Fagemo) | trade with Kings |
| 2019-06-22 | Canadiens | • 2020 fifth round pick (#135-Jakub Dobes) | • 2019 fifth round pick (#136-Henrik Rybinski) | trade with Panthers |
| 2019-06-22 | Canadiens | • 2020 fourth round pick (#95-Daniil Chechelev) | • 2019 fourth round pick (#108-Yegor Spiridonov) | trade with Sharks |
| 2019-06-22 | Canadiens | • Jayden Struble | 2019 NHL entry draft second round pick (#46 overall) | |
| 2019-06-22 | Canadiens | • Mattias Norlinder | 2019 NHL entry draft third round pick (#64 overall) | |
| 2019-06-22 | Canadiens | • Gianni Fairbrother | 2019 NHL entry draft third round pick (#77 overall) | |
| 2019-06-22 | Canadiens | • Jacob Leguerrier | 2019 NHL entry draft fifth round pick (#126 overall) | |
| 2019-06-22 | Canadiens | • Rhett Pitlick | 2019 NHL entry draft fifth round pick (#131 overall) | |
| 2019-06-22 | Canadiens | • Frederik Nissen Dichow / Frederik Dichow | 2019 NHL entry draft fifth round pick (#138 overall) | |
| 2019-06-22 | Canadiens | • Arsen Khisamutdinov | 2019 NHL entry draft sixth round pick (#170 overall) | |
| 2019-06-22 | Canadiens | • Rafael Harvey-Pinard | 2019 NHL entry draft seventh round pick (#201 overall) | |
| 2019-06-22 | Canadiens | • Kieran Ruscheinski | 2019 NHL entry draft seventh round pick (#206 overall) | |
| 2019-06-24 | Canadiens | • Mike Reilly (J.) | team tendered qualifying offer, making player a restricted free agent | |
| 2019-06-25 | Canadiens | • Brett Lernout | team declined to tender qualifying offer, making player an unrestricted free agent | |
| 2019-06-25 | Canadiens | • Daniel Audette | team declined to tender qualifying offer, making player an unrestricted free agent | |
| 2019-06-25 | Canadiens | • Hunter Shinkaruk | team declined to tender qualifying offer, making player an unrestricted free agent | |
| 2019-06-25 | Canadiens | • Artturi Lehkonen | team tendered qualifying offer, making player a restricted free agent | |
| 2019-06-25 | Canadiens | • Charles Hudon | team tendered qualifying offer, making player a restricted free agent | |
| 2019-06-25 | Canadiens | • Joel Armia | team tendered qualifying offer, making player a restricted free agent | |
| 2019-06-25 | Canadiens | • Michael McCarron | team tendered qualifying offer, making player a restricted free agent | |
| 2019-06-26 | Canadiens | • Mike Reilly (J.) | re-signed restricted free agent to a 2-year, $3M contract |
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