Virginia Cavs: every transfer in and out, fees paid and earned, squad market value.
| Date | Player | From | To | Fee |
|---|---|---|---|---|
| 2025-12-18 | Reese Miller | Virginia Cavs | Houston | Free |
| 2025-12-18 | Nicholas Simmonds | Virginia Cavs | Dallas | Free |
| 2025-03-11 | Nicholas Simmonds | Virginia Cavs | Charlottesville | Loan |
| 2025-01-01 | Nicholas Simmonds | Rich. Academy | Virginia Cavs | Free |
| 2022-08-18 | Oliver Gerbig | Virginia Cavs | Kitchee | Free |
| 2022-08-01 | Reese Miller | Houston Academy | Virginia Cavs | Free |
| 2020-02-29 | Oliver Gerbig | Coastal | Virginia Cavs | Free |
| 2020-01-10 | Joe Bell | Virginia Cavs | Viking FK | Free |
| 2020-01-09 | Henry Kessler | Virginia Cavs | New England | Free |
| 2019-05-01 | Henry Kessler | Virginia Cavs | Charlottesville | Loan |
| 2019-01-22 | Aboubacar Keita | Virginia Cavs | Columbus Crew | Free |
| 2018-08-01 | Aboubacar Keita | CLB Academy | Virginia Cavs | Free |
| 2018-05-01 | Henry Kessler | Virginia Cavs | Connecticut | Loan |
| 2018-01-01 | Faris Abdi | Virginia Cavs | Team Vaud U21 | — |
| 2017-08-01 | Joe Bell | Phoenix Res. | Virginia Cavs | Free |
| 2017-08-01 | Henry Kessler | Beachside SC | Virginia Cavs | Free |
| 2017-07-01 | Faris Abdi | IMG Soccer | Virginia Cavs | — |
| 2016-01-01 | Derrick Etienne Jr. | Virginia Cavs | New York | Free |
| 2015-08-01 | Derrick Etienne Jr. | NYRB Academy | Virginia Cavs | Free |
| 2014-08-01 | Jeff Gal | Virginia Cavs | Bridges FC | Free |