| Trans Num | Date | Details |
| 2021.1 | 2021-02-18 | Boston Red Sox trades Drew Smyly to the San Francisco Giants for Garrett Stubbs and SFG 2021 #2. |
| 2017.6 | 2017-01-17 | Tampa Bay trades Shin-Soo Choo, Alex Colome, Whit Merrifield, Drew Smyly, and TBR #1 to Texas for Nelson Cruz, Matt Bush, and Chi Chi Gonzalez. |
| 2015.28 | 2015-06-24 | Detroit trades Drew Smyly, Drew Storen, and Leonys Martin to Tampa Bay for Carlos Gonzalez, Shane Victorino, Joe Wieland, TBR 2016 #1, and TBR 2016 #3. |