Milan Michalek trades
| Ottawa Senators acquire | Date | Toronto Maple Leafs acquire | ||
|---|---|---|---|---|
 | Dion Phaneuf | February 9, 2016 | Jared Cowen |  |
| Matt Frattin | Colin Greening | |||
| Casey Bailey | Milan Michalek | |||
| Ryan Rupert | Tobias Lindberg | |||
| Cody Donaghey | 2017 2nd round pick | |||
| San Jose Sharks acquire | Date | Ottawa Senators acquire | ||
|---|---|---|---|---|
 | Dany Heatley | September 12, 2009 | Jonathan Cheechoo | |
| 2010 5th round pick (#136-Issac Macleod) | Milan Michalek | |||
| 2010 2nd round pick (#58-Kent Simpson) | ||||