Jim Rutherford trades
| Ottawa Senators acquire | Date | Pittsburgh Penguins acquire | ||
|---|---|---|---|---|
 | Matt Murray | October 7, 2020 | Jonathan Gruden |  |
| 2020 2nd round pick | ||||
| Pittsburgh Penguins acquire | Date | Florida Panthers acquire | ||
|---|---|---|---|---|
| Colton Sceviour | September 24, 2020 | Patric Hornqvist |  |
| Mike Matheson | ||||
| Minnesota Wild acquire | Date | Pittsburgh Penguins acquire | ||
|---|---|---|---|---|
 | Nick Bjugstad | September 11, 2020 | 2021 conditional 7th round pick | |
| Comment: The condition on the pick is dependent on the number of games that Bjugstad plays the following season for the Wild. | ||||
| Pittsburgh Penguins acquire | Date | Toronto Maple Leafs acquire | ||
|---|---|---|---|---|
| Kasperi Kapanen | August 25, 2020 | 2020 1st round pick |  |
| Pontus Aberg | Evan Rodrigues | |||
| Jesper Lindgren | Filip Hallander | |||
| David Warsofsky | ||||
| Pittsburgh Penguins acquire | Date | Buffalo Sabres acquire | ||
|---|---|---|---|---|
| Conor Sheary | February 24, 2020 | Dominik Kahun |  |
| Evan Rodrigues | ||||
| Pittsburgh Penguins acquire | Date | San Jose Sharks acquire | ||
|---|---|---|---|---|
| Patrick Marleau | February 24, 2020 | 2021 conditional 3rd round pick |  |
| Comment: 3rd pick becomes a 2nd rounder if the Penguins win the Stanley Cup. | ||||
| Montreal Canadiens acquire | Date | Pittsburgh Penguins acquire | ||
|---|---|---|---|---|
 | Jake Lucchini | February 20, 2020 | Phil Varone | |
| Joseph Blandisi | Riley Barber | |||
| Pittsburgh Penguins acquire | Date | Minnesota Wild acquire | ||
|---|---|---|---|---|
| Jason Zucker | February 10, 2020 | 2020 conditional 1st round pick | |
| Calen Addison | ||||
| Alex Galchenyuk | ||||
| Comment: Minnesota will receive Pittsburgh's own 1st round pick in the 2020 draft if the Penguins make the Stanley Cup Playoffs. If Pittsburgh does not qualify for the postseason, it will have the option to instead give Minnesota its 1st round pick in 2021. The option will expire at 5 p.m. ET on June 1 2020. | ||||
| Pittsburgh Penguins acquire | Date | Dallas Stars acquire | ||
|---|---|---|---|---|
| John Nyberg | January 17, 2020 | Oula Palve |  |
| Pittsburgh Penguins acquire | Date | Florida Panthers acquire | ||
|---|---|---|---|---|
| Kevin Roy | December 17, 2019 | Ryan Haggerty | |
| Chicago Blackhawks acquire | Date | Pittsburgh Penguins acquire | ||
|---|---|---|---|---|
 | Joseph Cramarossa | November 20, 2019 | Graham Knott | |
| Anaheim Ducks acquire | Date | Pittsburgh Penguins acquire | ||
|---|---|---|---|---|
 | Erik Gudbranson | October 25, 2019 | Andreas Martinsen | |
| 2021 7th round pick | ||||
| Pittsburgh Penguins acquire | Date | Edmonton Oilers acquire | ||
|---|---|---|---|---|
| John Marino | July 26, 2019 | 2021 conditional 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 | ||||
| Chicago Blackhawks acquire | Date | Pittsburgh Penguins acquire | ||
|---|---|---|---|---|
| Olli Maatta | June 15, 2019 | Dominik Kahun | |
| 2019 5th round pick | ||||
| Pittsburgh Penguins acquire | Date | Vancouver Canucks acquire | ||
|---|---|---|---|---|
| Erik Gudbranson | February 25, 2019 | Tanner Pearson |  |
| Pittsburgh Penguins acquire | Date | Florida Panthers acquire | ||
|---|---|---|---|---|
| Jean-Sebastien Dea | February 25, 2019 | Chris Wideman | |
| Pittsburgh Penguins acquire | Date | Columbus Blue Jackets acquire | ||
|---|---|---|---|---|
| Blake Siebenaler | February 11, 2019 | 2019 conditional 7th round pick |  |
| Pittsburgh Penguins acquire | Date | Florida Panthers acquire | ||
|---|---|---|---|---|
| Jared McCann | February 1, 2019 | 2019 4th round pick | |
| Nick Bjugstad | 2019 2nd round pick | |||
| Riley Sheahan | ||||
| Derick Brassard | ||||
| 2019 4th round pick | ||||
| Dallas Stars acquire | Date | Pittsburgh Penguins acquire | ||
|---|---|---|---|---|
| Jamie Oleksiak | January 28, 2019 | 2019 4th round pick | |