Chesterf. U18: every transfer in and out, fees paid and earned, squad market value.
| Date | Player | From | To | Fee |
|---|---|---|---|---|
| 2025-11-04 | James Sissons | Chesterf. U18 | Alfreton | Loan |
| 2025-08-22 | James Sissons | FC Melita U19 | Chesterf. U18 | Free |
| 2024-07-01 | Liam Jessop | Chesterf. U18 | Chesterfield | — |
| 2023-09-12 | Liam Jessop | Bruno's Magpies | Chesterf. U18 | Free |