Chesapeake Baysox Roster & Staff
Chesapeake Transactions
| Date | Transaction |
| 05/07/26 | Baltimore Orioles sent 2B Jackson Holliday on a rehab assignment to Chesapeake Baysox. |
| 05/07/26 | RHP Yaqui Rivera assigned to Chesapeake Baysox from Norfolk Tides. |
| 05/07/26 | RHP Alex Pham assigned to Chesapeake Baysox from Norfolk Tides. |
| 05/06/26 | Chesapeake Baysox placed RHP Blake Money on the full-season injured list. |
| 05/05/26 | RHP Christian Herberholz assigned to Chesapeake Baysox from Norfolk Tides. |
| 05/03/26 | RHP Jeisson Cabrera assigned to Chesapeake Baysox from Norfolk Tides. |
| 05/02/26 | Chesapeake Baysox sent RHP Bradley Brehmer on a rehab assignment to Delmarva Shorebirds. |
| 05/01/26 | Chesapeake Baysox activated RHP Juaron Watts-Brown from the 7-day injured list. |
| 05/01/26 | RHP Yaqui Rivera assigned to Norfolk Tides from Chesapeake Baysox. |
| 05/01/26 | RHP Jeisson Cabrera assigned to Norfolk Tides from Chesapeake Baysox. |
| 05/01/26 | RHP Christian Herberholz assigned to Norfolk Tides from Chesapeake Baysox. |
| 05/01/26 | RHP Trace Bright assigned to Norfolk Tides from Chesapeake Baysox. |
| 05/01/26 | LHP Juan Rojas assigned to Chesapeake Baysox from Frederick Keys. |