| Trans Num | Date | Details |
| 2020.4 | 2020-02-23 | Cleveland Indians trade Derek Holland and CLE 2020 #2 to the Pittsburgh Pirates for Enrique Hernandez. |
| 2019.4 | 2019-01-26 | Cleveland trades Sal Romano, Domingo German, Victor Robles, Yandy Diaz, Francisco Mejia, CLE 2019 #2, and CLE 2019 #3 to Texas for Derek Holland, Jose Leclerc, and George Springer. |