- Sept 28, 2009: Assigned Brad Marchand and Zach Hamill to Providence.
- Sept 26, 2009: Assigned Mikko Lehtonen, Jeff LoVecchio, Adam McQuaid, and Kirk MacDonald to Providence.
- Sept 26, 2009: Placed Dany Sabourin, Drew Fata, Guillaume Lefebvre, Trent Whitfield, Andy Wozniewski on waivers.
- Sept 26, 2009: Signed Guillaume Lefebvre to a one year contract.
- Sept 23, 2009: Sent Kevin Regan, Jeff Penner, Andrew Bodnarchuk, and Jamie Arneil to Providence.
- Sept 18, 2009: Traded forward Phil Kessel to Toronto for a 1st & 2nd round pick in 2010 and a 1st round pick in 2011.
- Sept 8, 2009: Signed defenseman Andy Wozniewski to a one-year contract.
- July 26, 2009: Signed defenseman Derek Morris to a one-year contract.
- July 20, 2009: Signed defenseman Matt Hunwick to a multi-year contract extension.
- July 14, 2009: Signed defensemen Rob Kwiet and Zach McKelvie, and centers Drew Larman and Trent Whitfield to one-year contracts.
- July 9, 2009: Signed goaltender Dany Sabourin and defenseman Drew Fata to one-year contracts.
- July 4, 2009: Signed right wing Mark Recchi to a one-year contract; right wing Byron Bitz to a multi-year contract; center Steve Begin to a one-year contract; defenseman Johnny Boychuck to a one-year contract.
- June 15, 2009: Signed general manager Peter Chiarelli to a multi-year contract extension.
