| Trans Num | Date | Details |
| 2021.9 | 2021-04-19 | Cleveland Indians trade Anthony Rendon and Dee Strange-Gordon to the Boston Midnight Riders for Andrew Benintendi and Keibert Ruiz. |
| 2020.22 | 2020-05-25 | Boston Midnight Riders trade Shin-Soo Choo, Oliver Drake, Lance Lynn, and Wade Miley to the Philadelphia Phillies for Kolby Allard, Andrew Benintendi, Andrew Heaney, and James Karinchak. |