| 10/8/2019 | Assigned F Gemel Smith to Syracuse (AHL). |
| 9/30/2019 | Assigned F Danick Martel, F Alexander Volkov and D Luke Schenn to Syracuse (AHL). |
| 9/22/2019 | Assigned F Alex Barre-Boulet, F Ross Colton, F Cory Conacher, F Chris Mueller, F Otto Somppi, F Mitchel Stephens and D Cal Foote to Syracuse (AHL). Assigned F Nolan Foote to Kelowna (WHL). |
| 9/21/2019 | Assigned F Jimmy Huntington, F Boris Katchouk, F Alexey Lipanov, F Ryan Lohin, F Taylor Raddysh, F Dennis Yan, D Oleg Sosunov and D Matt Spencer to Syracuse (AHL). |
| 9/18/2019 | Assigned F Gabriel Fortier to Baie-Comeau (QMJHL), F Maxim Cajkovic to Saint John (QMJHL), D Quinn Schmiemann to Kamloops (WHL). |
| 8/24/2019 | Signed F Pat Maroon to a one-year contract. |
| 8/24/2019 | Acquired a 2020 4th round pick from Detroit in exchange for F Adam Erne. |
| 8/5/2019 | Signed D Kevin Shattenkirk to a one-year contract. |
| 7/30/2019 | Acquired G Mike Condon and a 2020 6th round pick from Ottawa in exchange for F Ryan Callahan and a 2020 5th round pick. |
| 7/29/2019 | Re-signed G Andrei Vasilevskiy to an eight-year contract extension. |
| 7/17/2019 | Re-signed D Dominik Masin to a one-year, two-way contract. |
| 7/16/2019 | Re-signed D Ben Thomas to a one-year, two-way contract. |
| 7/9/2019 | Re-signed F Danick Martel to a one-year, two-way contract. |
| 7/8/2019 | Signed F Gemel Smith to a one-year, two-way contract. |
| 7/5/2019 | Re-signed F Cedric Paqeutte to a two-year contract. |
| 7/5/2019 | Re-signed F Carter Verhaeghe to a one-year, two-way contract. |
| 7/1/2019 | Signed F Chris Mueller to a one-year, two-way contract. |
| 7/1/2019 | Signed G Spencer Martin to a one-year, two-way contract. |
| 7/1/2019 | Signed G Scott Wedgewood to a one-year, two-way contract. |
| 7/1/2019 | Signed D Luke Witkowski to a two-year, two-way contract. |
| 7/1/2019 | Signed D Luke Schenn to a one-year contract |
| 7/1/2019 | Signed G Curtis McElhinney to a two-year contract. |
| 6/25/2019 | Signed F Nolan Foote to a three-year entry level contract. |
| 6/22/2019 | Acquired a 2019 3rd round pick, a conditional 2020 1st round pick and G Marek Mazanec from Vancouver in exchange for F J.T. Miller. |
| 6/19/2019 | Re-signed F Daniel Walcott to a one-year, two-way contract. |
| 6/18/2019 | Re-signed D Braydon Coburn to a two-year contract. |
| 6/14/2019 | Acquired a 2021 7th round pick from Nashville in exchange for G Connor Ingram. |
| 6/14/2019 | Re-signed D Cameron Gaunce to a one-year, two-way contract. |
| 5/3/2019 | Re-signed D Jan Rutta to a one-year contract. |
