| Trans Num | Date | Details |
| 2021.13 | 2021-06-14 | Philadelphia Phillies trade Alex Colome and Zach Eflin to the Baltimore Orioles for Jordan Montgomery and Ryan Pressly. |
| 2021.8 | 2021-04-17 | San Francisco Giants trade Ryan Pressly to the Baltimore Orioles for JoJo Romero and BAL 2022 #7. |
| 2020.8 | 2020-02-25 | San Francisco Giants trade Clay Buchholz and HOU 2020 #1 to the Toronto Mohawks for James Paxton and Ryan Pressly. |