Maryland (): varje in- och utgående övergång, betalda och intjänade summor, och truppens marknadsvärde.
| Datum | Spelare | Från | Till | Summa |
|---|---|---|---|---|
| 2023-12-19 | Kimani Stewart-Baynes | Maryland | Colorado | Fri |
| 2023-08-01 | Kimani Stewart-Baynes | Vaughan Azzurri | Maryland | Fri |
| 2023-02-02 | Griffin Dillon | Maryland | Real Monarchs | Fri |
| 2022-12-21 | Chris Rindov | Maryland | Kansas City | Fri |
| 2022-03-18 | Jacen Russell-Rowe | Maryland | Columbus 2 | Fri |
| 2022-01-11 | Ben Bender | Maryland | Charlotte | Fri |
| 2021-08-01 | Griffin Dillon | RSL Academy | Maryland | Fri |
| 2021-05-01 | Ben Bender | Maryland | Baltimore | Lån |
| 2020-08-01 | Ben Bender | Baltimore | Maryland | Fri |
| 2020-08-01 | Jacen Russell-Rowe | TFC Academy | Maryland | Fri |
| 2019-08-01 | Chris Rindov | Bethesda-Olney | Maryland | Fri |
| 2019-01-22 | Donovan Pines | Maryland | D.C. United | Fri |
| 2019-01-11 | Amar Sejdić | Maryland | Montreal | Fri |
| 2019-01-11 | Dayne St. Clair | Maryland | Minnesota | Fri |
| 2018-05-01 | Amar Sejdić | Maryland | Derby City | Lån |
| 2018-05-01 | Dayne St. Clair | Maryland | NYRB U-23 | Lån |
| 2017-05-01 | Amar Sejdić | Maryland | Derby City | Lån |
| 2017-05-01 | Dayne St. Clair | Maryland | K-W United | Lån |
| 2016-08-01 | Donovan Pines | D.C. United Ac. | Maryland | Fri |
| 2016-05-01 | Dayne St. Clair | Maryland | K-W United | Lån |