Vaughan Azzurri: every transfer in and out, fees paid and earned, squad market value.
| Date | Player | From | To | Fee |
|---|---|---|---|---|
| 2023-08-01 | Kimani Stewart-Baynes | Vaughan Azzurri | Maryland | Free |
| 2023-03-12 | Kimani Stewart-Baynes | Vaughan Azzurri | HFX Wanderers | Loan |
| 2022-02-16 | Niko Sigur | Vaughan Azzurri | NK Radomlje U19 | — |
| 2021-01-01 | Niko Sigur | Whitecaps Res. | Vaughan Azzurri | — |
| 2020-08-01 | Sidney Paris | Vaughan Azzurri | Navy Midshipmen | Free |
| 2019-10-14 | Promise David | Vaughan Azzurri | NK Trnje Zagreb | Free |
| 2019-08-01 | Ryan Raposo | Vaughan Azzurri | Syracuse | Free |
| 2019-07-01 | Sidney Paris | TFC Academy | Vaughan Azzurri | Free |
| 2019-05-01 | Alistair Johnston | Wake Forest | Vaughan Azzurri | Loan |
| 2018-08-01 | Ryan Raposo | Vaughan Azzurri | Syracuse | Loan |
| 2018-07-31 | Alistair Johnston | Vaughan Azzurri | Red Storm | Free |
| 2017-08-01 | Alistair Johnston | Vaughan Azzurri | Red Storm | Loan |
| 2016-08-01 | Alistair Johnston | Vaughan Azzurri | Red Storm | Loan |
| 2016-01-01 | Promise David | TFC Academy | Vaughan Azzurri | Free |
| 2016-01-01 | Alistair Johnston | Vaughan Azzurri | Red Storm | Loan |
| 2015-07-01 | Ryan Raposo | Burlington SC | Vaughan Azzurri | Free |
| 2015-02-01 | Kosi Thompson | Vaughan Azzurri | TFC Academy | Free |
| 2015-01-01 | Alistair Johnston | ANB Futbol | Vaughan Azzurri | Free |