| August 6 | | |
 | D Trevor Carrick |  | D Kyle Wood |
| July 30 | | |
 | F Ryan Callahan
2020 5th-round pick |  | G Mike Condon
2020 6th-round pick |
| July 29 | | |
 | F Nikita Gusev |  | 2020 3rd-round pick
2021 2nd-round pick |
| July 26 | | |
 | D John Marino |  | 2021 6th-round pick* |
| July 25 | | |
 | D Jordan Schmaltz |  | D Andreas Borgman |
| July 23 | | |
| F David Clarkson
2020 4th-round pick | | G Garret Sparks |
| July 19 | | |
| F James Neal |  | F Milan Lucic
2020 3rd-round pick* |
| July 16 | | |
 | F Zack Smith | | F Artem Anisimov |
| July 9 | | |
| F Alexander Nylander |  | D Henri Jokiharju |
| July 1 | | |
| F Jimmy Vesey |  | 2021 3rd-round pick |
| D Nikita Zaitsev
F Connor Brown
F Michael Carcone | | D Cody Ceci
D Ben Harpur
F Aaron Luchuk
2020 3rd-round pick |
| June 30 | | |
 | F Nicolas Deslauriers |  | 2020 4th-round pick |
| F Andrew Shaw
2021 7th-round pick | | 2020 2nd-round pick
2020 7th-round pick
2021 3rd-round pick |
| G James Reimer |  | G Scott Darling
2020 6th-round pick |
| June 29 | | |
 | F Phil Kessel
D Dane Birks
2021 4th-round pick | | F Alex Galchenyuk
D Pierre-Olivier Joseph |
 | D Jacob MacDonald | | F Dominic Toninato |
| June 28 | | |
| F Andre Burakovsky |  | F Scott Kosmachuk
2020 2nd-round pick
2020 3rd-round pick |
| D Colin Miller | | 2021 2nd-round pick
2022 5th-round pick |
| June 27 | | |
| F Erik Haula | | F Nicolas Roy
2021 5th-round pick* |
| June 25 | | |
| F Carl Soderberg | | D Kevin Connauton
2020 3rd-round pick |
| June 24 | | |
| D Calvin de Haan
F Aleksi Saarela | | G Anton Forsberg
D Gustav Forsling |
 | F Tyler Pitlick |  | F Ryan Hartman |
| June 22 | | |
| No. 211 pick | | 2020 7th-round pick |
| No. 208 pick | | 2020 7th-round pick |
| No. 201 pick | | 2020 7th-round pick |
| No. 153 pick | | No. 211 pick
2020 7th-round pick |
| No. 143 pick |  | No. 177 pick
No. 191 pick |
| No. 136 pick | | 2020 5th-round pick |
| No. 108 pick | | 2020 4th-round pick |
| No. 102 pick |  | No. 122 pick
No. 175 pick |
| F Francis Perron
No. 215 pick | | F Tom Pyatt
No. 164 pick |
| No. 91 pick | | No. 118 pick
No. 129 pick |
| No. 81 pick |  | No. 104 pick
No. 114 pick |
 | No. 75 pick |  | 2020 3rd-round pick |
| No. 74 pick | | No. 98 pick
No. 151 pick
No. 207 pick |
| No. 59 pick | | No. 73 pick
No. 99 pick |
| No. 55 pick | | No. 82 pick
No. 91 pick |
 | No. 50 pick | | No. 64 pick
No. 126 pick |
| No. 41 pick | | No. 48 pick
No. 82 pick |
| F John Hayden | | F John Quenneville |
| F J.T. Miller | | G Marek Mazanec
No. 71 pick
2020 1st-round pick* |
| No. 37 pick | | No. 44 pick
No. 83 pick |
| No. 34 pick | | No. 45 pick
No. 65 pick |
| D P.K. Subban | | D Steve Santini
D Jeremy Davies
2019 2nd-round pick
2020 2nd-round pick |
| F Patrick Marleau
2020 1st-round pick*
2020 7th-round pick | | 2020 6th-round pick |
| June 21 | | |
| No. 11 pick | | No. 14 pick
No. 45 pick |
| June 18 | | |
| D Justin Braun | | 2019 2nd-round pick
2020 3rd-round pick |
| June 17 | | |
| D Jacob Trouba |  | D Neal Pionk
2019 1st-round pick |
| June 15 | | |
| D Olli Maatta | | F Dominik Kahun
2019 5th-round pick (TB) |
| June 14 | | |
| D Radko Gudas | | D Matt Niskanen |
| G Connor Ingram | | 2021 7th-round pick |
| June 3 | | |
| F Kevin Hayes | | 2019 5th-round pick |
| May 30 | | |
| 2019 7th-round pick* | | D Fedor Gordeev |
| Apr. 30 | | |
| D Adam Fox | | 2019 2nd-round pick
2020 3rd-round pick* |
| Feb. 25 | | |
| F Alex Broadhurst | | Future considerations |
| D Chris Wideman | | F Jean-Sebastien Dea |
| F Nic Petan | | F Par Lindholm |
| F Linus Karlsson | | F Jonathan Dahlen |
| D Bogdan Kiselevich | | 2021 7th-round pick |
| D Nathan Beaulieu | | 2019 6th-round pick |
| D Erik Gudbranson | | F Tanner Pearson |
| F Matt Hendricks | | 2020 7th-round pick |
 | F Marcus Johansson | | 2019 2nd-round pick
2020 4th-round pick |
| F Wayne Simmonds | | F Ryan Hartman
2020 4th-round pick* |
| D Michael Del Zotto | | 2019 6th-round pick |
| F Mark Stone
F Tobias Lindberg | | D Erik Brannstrom
F Oscar Lindberg
2020 2nd-round pick (DAL) |
| F Mikael Granlund | | F Kevin Fiala |
| D Oscar Fantenberg | | 2020 4th-round pick* |
| D Adam McQuaid | | 2019 4th-round pick
2019 7th-round pick |
| F Derick Brassard
2020 6th-round pick* | | 2020 3rd-round pick |
| F Tomas Jurco | | Future considerations |
| F Cliff Pu | | Future considerations |
| F Jordan Weal | | F Michael Chaput |
| F Kevin Hayes | | F Brendan Lemieux
2019 1st-round pick
2022 4th-round pick* |
| G Keith Kinkaid | | 2022 5th-round pick |
| F Brian Gibbons | | D Patrick Sieloff |
| Feb. 24 | | |
| F Gustav Nyquist | | 2019 second-round pick*
2020 third-round pick* |
| D Brandon Montour | | F Brendan Guhle
2019 1st-round pick (SJ/STL) |
| F Spencer Watson | | F Matheson Iacopelli |
| F Nicholas Baptiste | | Future considerations |
| Feb. 23 | | |
| F Mats Zuccarello | | 2019 2nd-round pick*
2020 3rd-round pick* |
| F Ryan Dzingel
2019 7th-round pick (CGY) | | F Anthony Duclair
2020 2nd-round pick
2021 2nd-round pick |
| D Ben Lovejoy | | D Connor Carrick
2019 3rd-round pick |
| Feb. 22 | | |
| F Matt Duchene
D Julius Bergman | | F Vitaly Abramov
F Jonathan Davidsson
2019 1st-round pick
2020 1st-round pick* |
| D Nick Jensen
2019 5th-round pick (BUF) | | D Madison Bowey
2020 2nd-round pick |
| F Vincent Praplan | | Future considerations |
| Feb. 21 | | |
| F Carl Hagelin | | 2019 3rd-round pick
2020 6th-round pick* |
| Feb. 20 | | |
| F Charlie Coyle | | F Ryan Donato
2019 5th-round pick |
| Feb. 18 | | |
| F Peter Holland | | D Darren Raddysh |
| Feb. 16 | | |
| F Sam Gagner | | F Ryan Spooner |
| G Cam Talbot | | G Anthony Stolarz |
| Feb. 12 | | |
| G Marek Mazanec | | 2020 7th-round pick |
| Feb. 11 | | |
| D Blake Siebnaler | | 2019 7th-round pick* |
| F Nate Thompson
2019 5th-round pick | | 2019 4th-round pick |
| Feb. 9 | | |
| F Dale Weise
D Christian Folin | | D David Schlemko
F Byron Froese |
| Feb. 8 | | |
| F Emil Pettersson | | F Adam Helewka
F Laurent Dauphin |
| Feb. 6 | | |
| F Cody McLeod | | 2020 7th-round pick |
| F Brian Boyle | | 2019 2nd-round pick |
| F Jean-Christophe Beaudin | | F Max McCormick |
| Feb. 1 | | |
| F Derick Brassard
F Riley Sheahan
2019 2nd-round pick
2019 4th-round pick
2019 4th-round pick (MIN) | | F Nick Bjugstad
F Jared McCann |
| Jan. 30 | | |
| D Michael Kapla | | D Ryan Murphy |
| Jan. 28 | | |
| D Jake Muzzin | | F Carl Grundstrom
D Sean Durzi
2019 1st-round pick |
| D Jamie Oleksiak | | 2019 4th-round pick |
| Jan. 21 | | |
| D Brad Hunt
2019 6th-round pick | | 2019 5th-round pick* |
| Jan. 17 | | |
| F Taylor Leier | | F Justin Bailey |
| F Nino Niederreiter | | F Victor Rask |
| F Derek Grant | | F Joseph Blandisi |
| D Michael Del Zotto | | D Luke Schenn
2020 7th-round pick |
| Jan. 16 | | |
| F Pontus Aberg | | F Justin Kloos |
| Jan. 14 | | |
| F Connor Brickley | | F Cole Schneider |
| F Andrew Cogliano | | F Devin Shore |
| Jan. 11 | | |
| D Slater Koekkoek
2019 5th-round pick | | D Jan Rutta
2019 7th-round pick |
| F Jordan Weal | | 2019 6th-round pick |
| D Cody Goloubef | | F Paul Carey |
| F Morgan Klimchuk | | F Gabriel Gagne |
| Jan. 3 | | |
| D Jimmy Oligny | | Future considerations |
| G Jared Coreau | | Future considerations |
| Jan. 2 | | |
| G Anders Nilsson
F Darren Archibald | | G Mike McKenna
F Tom Pyatt
2019 6th-round pick |
| Dec. 30 | | |
| D Brandon Manning
D Robin Norelli | | F Drake Caggiula
D Jason Garrison |
| D Alex Petrovic | | D Chris Wideman
2019 3rd-round pick* |
| Dec. 29 | | |
| G Michael Hutchinson | | 2020 5th-round pick |
| Dec. 28 | | |
| F Giovanni Fiore | | D Trevor Murphy |
| Dec. 10 | | |
| D Steve Oleksy | | F Adam Cracknell |
| Dec. 5 | | |
| D Stefan Elliott
F Tobias Lindberg | | D Macoy Erkamps
F Ben Sexton |
| Dec. 3 | | |
| F Daniel Sprong | | D Marcus Pettersson |
| F Josh Leivo | | F Michael Carcone |
| Nov. 27 | | |
| F Morgan Klimchuk | | D Andrew Nielsen |
| Nov. 25 | | |
| F Nick Schmaltz | | F Dylan Strome
F Brendan Perlini |
| Nov. 22 | | |
| D Chris Wideman | | 2020 6th-round pick |
| Nov. 21 | | |
| F Pavel Jenys | | D Stepan Falkovsky |
| Nov. 16 | | |
| F Ryan Strome | | F Ryan Spooner |
| Nov. 14 | | |
| F Tanner Pearson | | F Carl Hagelin |
| Nov. 10 | | |
| D Taylor Fedun | | 2020 7th-round pick* |
| Oct. 18 | | |
| F Mitch Hults | | Future considerations |
| Oct. 3 | | |
| D Gustav Olofsson | | F William Bitten |
| Oct. 1 | | |
| D Jack Dougherty | | F Nicholas Baptiste |
| D Brett Kulak | | D Matt Taormina
D Rinat Valiev |
| D Connor Carrick | | 2019 7th-round pick* |
| Sept. 13 | | |
| D Erik Karlsson
F Francis Perron | | F Josh Norris
F Chris Tierney
F Rudolfs Balcers
D Dylan DeMelo
2020 1st-round pick*
2019 2nd-round pick*
2021 2nd-round pick* |
| Sept. 11 | | |
| D Adam McQuaid | | D Steven Kampfer
2019 4th-round pick
2019 7th-round pick* |
| Sept. 10 | | |
| F Max Pacioretty | | F Tomas Tatar
F Nick Suzuki
2019 2nd-round pick |
