All countries
| 34. Round | Gillingham | Oldham | 0:3 (0:2, 0:1) | details | 21.02.2026 | |||
| 33. Round | Chesterfield | Gillingham | 1:0 (1:0, 0:0) | details | 17.02.2026 | |||
| 32. Round | Crewe | Gillingham | 1:0 (0:0, 1:0) | details | 14.02.2026 | |||
| 31. Round | Gillingham | Tranmere | 2:1 (1:0, 1:1) | details | 07.02.2026 | |||
| 25. Round | Notts Co | Gillingham | 1:0 (1:0, 0:0) | details | 03.02.2026 | |||
| 30. Round | Gillingham | Bromley | 1:4 (1:3, 0:1) | details | 31.01.2026 | |||
| 28. Round | Harrogate | Gillingham | 0:3 (0:0, 0:3) | details | 24.01.2026 | |||
| 27. Round | Gillingham | Newport | 3:2 (1:1, 2:1) | details | 17.01.2026 | |||
| 24. Round | Swindon | Gillingham | 2:0 (0:0, 2:0) | details | 01.01.2026 | |||
| 23. Round | Gillingham | Colchester | 1:1 (0:0, 1:1) | details | 29.12.2025 | |||
| 22. Round | Gillingham | Cambridge Utd | 1:1 (0:1, 1:0) | details | 26.12.2025 | |||
| 21. Round | Fleetwood | Gillingham | 2:1 (0:1, 2:0) | details | 20.12.2025 | |||
| 20. Round | Gillingham | Barrow | 2:2 (2:0, 0:2) | details | 13.12.2025 | |||
| 19. Round | Colchester | Gillingham | 0:0 (0:0, 0:0) | details | 06.12.2025 | |||
| 18. Round | Shrewsbury | Gillingham | 3:3 (3:1, 0:2) | details | 29.11.2025 | |||
| 17. Round | Gillingham | Barnet | 1:1 (1:1, 0:0) | details | 22.11.2025 | |||
| 16. Round | Gillingham | Crawley | 2:2 (1:0, 1:2) | details | 15.11.2025 | |||
| Group 15 | Gillingham | Wycombe | 0:3 (0:1, 0:2) | details | 11.11.2025 | |||
| 15. Round | Bristol Rovers | Gillingham | 0:1 (0:0, 0:1) | details | 08.11.2025 | |||
| 1/128-finals | Newport | Gillingham | 3:2 AfP (1:1, 0:0, 1:1, 4:3) | details | 01.11.2025 | |||
| 14. Round | Gillingham | Salford | 1:2 (1:2, 0:0) | details | 25.10.2025 | |||
| 13. Round | Grimsby | Gillingham | 1:0 (0:0, 1:0) | details | 18.10.2025 | |||
| 12. Round | Gillingham | Cheltenham | 1:1 (0:0, 1:1) | details | 11.10.2025 | |||
| Group 15 | Colchester | Gillingham | 2:1 (0:1, 2:0) | details | 07.10.2025 | |||
| 11. Round | MK Dons | Gillingham | 3:2 (1:0, 2:2) | details | 04.10.2025 | |||
| 10. Round | Gillingham | Harrogate | 0:1 (0:1, 0:0) | details | 27.09.2025 | |||
| 9. Round | Newport | Gillingham | 1:3 (1:3, 0:0) | details | 20.09.2025 | |||
| 8. Round | Gillingham | Notts Co | 1:0 (0:0, 1:0) | details | 13.09.2025 | |||
| 7. Round | Bromley | Gillingham | 2:2 (2:0, 0:2) | details | 06.09.2025 | |||
| Group 15 | Gillingham | Fulham U21 | 4:1 (1:0, 3:1) | details | 02.09.2025 | |||
| 6. Round | Oldham | Gillingham | 0:1 (0:0, 0:1) | details | 30.08.2025 | |||
| 5. Round | Gillingham | Crewe | 1:0 (0:0, 1:0) | details | 23.08.2025 | |||
| 4. Round | Gillingham | Chesterfield | 4:1 (1:0, 3:1) | details | 19.08.2025 | |||
| 3. Round | Tranmere | Gillingham | 1:1 (0:0, 1:1) | details | 16.08.2025 | |||
| 1/64-finals | Gillingham | AFC Wimbledon | 1:2 AfP (0:1, 1:0, 2:4) | details | 12.08.2025 | |||
| 2. Round | Gillingham | Walsall | 1:0 (0:0, 1:0) | details | 09.08.2025 | |||
| 1. Round | Accrington | Gillingham | 1:1 (0:0, 1:1) | details | 02.08.2025 | |||
| Dartford | Gillingham | 0:2 (0:2, 0:0) | details | 26.07.2025 | ||||
| Chatham | Gillingham | 1:0 (1:0, 0:0) | details | 25.07.2025 | ||||
| Ebbsfleet | Gillingham | 2:1 (1:0, 1:1) | details | 22.07.2025 | ||||
| Gillingham | Luton | 0:2 (0:2, 0:0) | details | 19.07.2025 | ||||
| Gillingham | Reading | 0:0 (0:0, 0:0) | details | 12.07.2025 | ||||
| Dover | Gillingham | 0:1 (0:1, 0:0) | details | 08.07.2025 | ||||
| 46. Round | Port Vale | Gillingham | 0:1 (0:0, 0:1) | details | 03.05.2025 | |||
| 45. Round | Gillingham | Swindon | 1:1 (0:0, 1:1) | details | 26.04.2025 | |||
| 44. Round | Gillingham | AFC Wimbledon | 1:0 (0:0, 1:0) | details | 21.04.2025 | |||
| 43. Round | Cheltenham | Gillingham | 1:1 (1:1, 0:0) | details | 18.04.2025 | |||
| 42. Round | Gillingham | MK Dons | 1:0 (0:0, 1:0) | details | 12.04.2025 | |||
| 25. Round | Chesterfield | Gillingham | 1:1 (0:1, 1:0) | details | 08.04.2025 | |||
| 41. Round | Salford | Gillingham | 2:2 (2:2, 0:0) | details | 05.04.2025 | |||