Ray Shero trades
| San Jose Sharks acquire | Date | Pittsburgh Penguins acquire | ||
|---|---|---|---|---|
 | 2010 7th round pick (#200-Christopher Crane) | June 26, 2010 | 2011 7th round pick (#208-Scott Wilson) |  |
| Pittsburgh Penguins acquire | Date | Philadelphia Flyers acquire | ||
|---|---|---|---|---|
| rights to Dan Hamhuis | June 25, 2010 | 2011 3rd round pick (#83-Harrison Ruopp) |  |
| Anaheim Ducks acquire | Date | Pittsburgh Penguins acquire | ||
|---|---|---|---|---|
 | 2010 6th round pick (#177-Kevin Lind) | May 28, 2010 | rights to Mattias Modig | |
| Toronto Maple Leafs acquire | Date | Pittsburgh Penguins acquire | ||
|---|---|---|---|---|
 | Chris Peluso | March 3, 2010 | 2010 6th round pick (#152-Joe Rogalski) | |
| Toronto Maple Leafs acquire | Date | Pittsburgh Penguins acquire | ||
|---|---|---|---|---|
| Luca Caputi | March 2, 2010 | Alexei Ponikarovsky | |
| Martin Skoula | ||||
| Florida Panthers acquire | Date | Pittsburgh Penguins acquire | ||
|---|---|---|---|---|
 | 2010 2nd round pick (#50-Connor Brickley) | March 1, 2010 | Jordan Leopold | |
| St. Louis Blues acquire | Date | Pittsburgh Penguins acquire | ||
|---|---|---|---|---|
 | Nate Guenin | February 11, 2010 | Steve Wagner | |
| Montreal Canadiens acquire | Date | Pittsburgh Penguins acquire | ||
|---|---|---|---|---|
 | 2009 7th round pick (#210-Petteri Simila) | June 27, 2009 | 2010 6th round pick (#177-Kevin Lind) | |
| Pittsburgh Penguins acquire | Date | New York Rangers acquire | ||
|---|---|---|---|---|
| 2009 5th round pick (#150-Andy (Grandson) Bathgate) | June 27, 2009 | Chad Johnson |  |
| Pittsburgh Penguins acquire | Date | New York Islanders acquire | ||
|---|---|---|---|---|
| Bill Guerin | March 4, 2009 | 2009 conditional 5th round pick (4th round if Penguins make 2009 playoffs 3rd round if Penguins advance to 2nd round of 2009 playoffs) (#91-Michael Lee) |  |
| St. Louis Blues acquire | Date | Pittsburgh Penguins acquire | ||
|---|---|---|---|---|
| Danny Richmond | March 4, 2009 | Andy Wozniewski | |
| Anaheim Ducks acquire | Date | Pittsburgh Penguins acquire | ||
|---|---|---|---|---|
| Ryan Whitney | February 26, 2009 | Chris Kunitz | |
| Eric Tangradi | ||||
| Edmonton Oilers acquire | Date | Pittsburgh Penguins acquire | ||
|---|---|---|---|---|
 | Dany Sabourin | January 17, 2009 | Mathieu Garon | |
| Ryan Stone | ||||
| 2011 4th round pick (#113-Tobias Rieder) | ||||
| Montreal Canadiens acquire | Date | Pittsburgh Penguins acquire | ||
|---|---|---|---|---|
| T.J. Kemp | January 5, 2009 | 2010 conditional 7th round pick (not exercised) | |
| St. Louis Blues acquire | Date | Pittsburgh Penguins acquire | ||
|---|---|---|---|---|
| Jonathan Filewich | December 19, 2008 | 2010 conditional 6th round pick (not exercised) | |
| Dallas Stars acquire | Date | Pittsburgh Penguins acquire | ||
|---|---|---|---|---|
 | Darryl Sydor | November 16, 2008 | Philippe Boucher | |
| Arizona Coyotes acquire | Date | Pittsburgh Penguins acquire | ||
|---|---|---|---|---|
 | future considerations | October 9, 2008 | Mike Zigomanis | |
| Tampa Bay Lightning acquire | Date | Pittsburgh Penguins acquire | ||
|---|---|---|---|---|
 | Michal Sersen | October 1, 2008 | 2009 5th round pick (#122-Alex Velischek) | |
| Chicago Blackhawks acquire | Date | Pittsburgh Penguins acquire | ||
|---|---|---|---|---|
 | Tim Brent | July 17, 2008 | Danny Richmond | |
| Tampa Bay Lightning acquire | Date | Pittsburgh Penguins acquire | ||
|---|---|---|---|---|
| Gary Roberts | June 28, 2008 | 2009 conditional 4th round pick (3rd round if Malone re-signs with Lightning) (#63-Ben Hanowski) | |
| rights to Ryan Malone | ||||