Annan Athletic: every transfer in and out, fees paid and earned, squad market value.
| Date | Player | From | To | Fee |
|---|---|---|---|---|
| 2025-05-31 | Luca Ross | Annan Athletic | Motherwell FC | Free |
| 2025-01-31 | Aaron Brown | Kilmarnock B | Annan Athletic | Loan |
| 2024-08-30 | Luca Ross | Motherwell B | Annan Athletic | Free |
| 2024-07-13 | Aaron Quigg | Kilmarnock B | Annan Athletic | Free |
| 2024-07-01 | Jamie Smith | Hamilton Acad. | Annan Athletic | Loan |
| 2024-03-01 | Aaron Brown | Kilmarnock B | Annan Athletic | Loan |
| 2024-02-01 | Michael Ndiweni | Newcastle U21 | Annan Athletic | Loan |
| 2021-04-24 | Ross Munro | Ross County | Annan Athletic | Loan |