Notable deals
| Montreal Canadiens acquire | Date | Buffalo Sabres acquire | ||
|---|---|---|---|---|
 | Marco Scandella | January 2, 2020 | 2020 4th round pick |  |
| Arizona Coyotes acquire | Date | New Jersey Devils acquire | ||
|---|---|---|---|---|
 | Taylor Hall | December 16, 2019 | Nate Schnarr |  |
| Blake Speers | Nick Merkley | |||
| Kevin Bahl | ||||
| 2020 conditional 1st round pick | ||||
| 2021 conditional 3rd round pick | ||||
| Comment: The 2020 first-round pick from Arizona in the Taylor Hall trade is top-three protected. Converts to 2021, if so. The conditions on the 2021 pick are as follows: the third-round pick in 2021 becomes a second-round selection if Arizona wins a Stanley Cup Playoff round OR Taylor Hall re-signs in Arizona. The third-round pick in 2021 becomes a first-round selection if Arizona wins a Stanley Cup Playoff round AND Taylor Hall re-signs in Arizona. If neither condition happens, New Jersey still receives the 2021 third-round pick. | ||||
| Vegas Golden Knights acquire | Date | Washington Capitals acquire | ||
|---|---|---|---|---|
 | Chandler Stephenson | December 2, 2019 | 2021 5th round pick |  |
| Detroit Red Wings acquire | Date | St. Louis Blues acquire | ||
|---|---|---|---|---|
 | Robby Fabbri | November 6, 2019 | Jacob De La Rose |  |
| Detroit Red Wings acquire | Date | Chicago Blackhawks acquire | ||
|---|---|---|---|---|
| Brendan Perlini | October 28, 2019 | Alec Regula |  |
| Ottawa Senators acquire | Date | New York Rangers acquire | ||
|---|---|---|---|---|
 | Vladislav Namestnikov | October 7, 2019 | Nick Ebert |  |
| 2021 4th round pick | ||||
| St. Louis Blues acquire | Date | Carolina Hurricanes acquire | ||
|---|---|---|---|---|
| Justin Faulk | September 24, 2019 | Joel Edmundson |  |
| 2020 5th round pick | Dominik Bokk | |||
| 2021 7th round pick | ||||
| New Jersey Devils acquire | Date | Vegas Golden Knights acquire | ||
|---|---|---|---|---|
| Nikita Gusev | July 29, 2019 | 2020 3rd round pick | |
| 2021 2nd round pick | ||||
| Calgary Flames acquire | Date | Edmonton Oilers acquire | ||
|---|---|---|---|---|
 | Milan Lucic | July 19, 2019 | James Neal |  |
| 2020 3rd round pick | ||||
| Chicago Blackhawks acquire | Date | Ottawa Senators acquire | ||
|---|---|---|---|---|
| Zack Smith | July 16, 2019 | Artem Anisimov | |
| Buffalo Sabres acquire | Date | Chicago Blackhawks acquire | ||
|---|---|---|---|---|
| Henri Jokiharju | July 9, 2019 | Alexander Nylander | |
| Ottawa Senators acquire | Date | Toronto Maple Leafs acquire | ||
|---|---|---|---|---|
| Nikita Zaitsev | July 1, 2019 | Cody Ceci |  |
| Connor Brown | Ben Harpur | |||
| Michael Carcone | Aaron Luchuk | |||
| 2020 3rd round pick | ||||
| Buffalo Sabres acquire | Date | New York Rangers acquire | ||
|---|---|---|---|---|
| Jimmy Vesey | July 1, 2019 | 2021 3rd round pick | |
| Toronto Maple Leafs acquire | Date | Colorado Avalanche acquire | ||
|---|---|---|---|---|
| Tyson Barrie | July 1, 2019 | Nazem Kadri |  |
| Alex Kerfoot | Calle Rosen | |||
| 2020 6th round pick | 2020 3rd round pick | |||
| Chicago Blackhawks acquire | Date | Montreal Canadiens acquire | ||
|---|---|---|---|---|
| Andrew Shaw | June 30, 2019 | 2020 2nd round pick | |
| 2021 7th round pick | 2020 7th round pick | |||
| 2021 3rd round pick | ||||
| Carolina Hurricanes acquire | Date | Florida Panthers acquire | ||
|---|---|---|---|---|
| James Reimer | June 30, 2019 | Scott Darling |  |
| 2020 6th round pick | ||||
| Pittsburgh Penguins acquire | Date | Arizona Coyotes acquire | ||
|---|---|---|---|---|
 | Alex Galchenyuk | June 29, 2019 | Phil Kessel | |
| Pierre-Olivier Joseph | Dane Birks | |||
| 2021 4th round pick | ||||
| Buffalo Sabres acquire | Date | Vegas Golden Knights acquire | ||
|---|---|---|---|---|
| Colin Miller | June 28, 2019 | 2021 2nd round pick | |
| 2022 5th round pick | ||||
| Colorado Avalanche acquire | Date | Washington Capitals acquire | ||
|---|---|---|---|---|
| Andre Burakovsky | June 28, 2019 | Scott Kosmachuk | |
| 2020 2nd round pick | ||||
| 2020 3rd round pick | ||||
| Carolina Hurricanes acquire | Date | Vegas Golden Knights acquire | ||
|---|---|---|---|---|
| Erik Haula | June 27, 2019 | Nicolas Roy | |
| 2021 conditional 5th round pick | ||||