| Date | Step H | Home | HS | – | AS | Away | Step A |
|---|---|---|---|---|---|---|---|
| Prelim | |||||||
| Sun, Sep 15, 2024 | Sleetmoor United | 9 | – | 1 | Allenton United | ||
| Round 1 | |||||||
| Sun, Oct 20, 2024 | Aston Village | 0 | – | 4 | Hilton Harriers | ||
| Sun, Oct 20, 2024 | Bakewell Town | 0 | – | 2 | Barlborough Juniors | ||
| Sun, Oct 20, 2024 | 6 | Belper Town | 15 | – | 1 | Pride Park Development | |
| Sun, Oct 20, 2024 | Borrowash Victoria | 6 | – | 0 | Belper Town Development | ||
| Sun, Oct 20, 2024 | Chesterfield U23s | w/o | – | Gresley Rovers | |||
| Sun, Oct 20, 2024 | Chesterfield Youth | 2 | – | 1 | Sleetmoor United | ||
| Sun, Oct 20, 2024 | Duffield Dynamo | 0p | – | 0 | Stapenhill | ||
| Sun, Oct 20, 2024 | 5 | Ilkeston Town | 18 | – | 0 | Hatton United | |
| Sun, Oct 20, 2024 | Long Earon United | 9 | – | 0 | Borrowash Victoria Reserves | ||
| Sun, Oct 20, 2024 | Matlock Town | 3 | – | 0 | Glossop North End | ||
| Sun, Oct 20, 2024 | Pride Park | 1 | – | 5 | Draycott Victoria | ||
| Sun, Oct 20, 2024 | Stanton Ilkeston | 0 | – | 9 | Buxton | 6 | |
| Sun, Oct 20, 2024 | Staveley Miners Welfare | 2 | – | 12 | Chesterfield Ladies | ||
| Sun, Oct 27, 2024 | Buxton Juniors | 4 | – | 0 | Ashbourne | ||
| Sun, Oct 27, 2024 | Gresley Rovers | 0 | – | 15 | Wirkworth Colts | ||
| Round 2 | |||||||
| Sun, Nov 17, 2024 | Barlborough Juniors | 0 | – | 7 | Chesterfield U23s | ||
| Sun, Nov 17, 2024 | 6 | Buxton | 0 | – | 5 | Chesterfield Ladies | |
| Sun, Nov 17, 2024 | Buxton Juniors | 1 | – | 7 | Draycott Victoria | ||
| Sun, Nov 17, 2024 | Derby County U21s | 6 | – | 0 | Chesterfield Youth | ||
| Sun, Nov 17, 2024 | Duffield Dynamo | 1 | – | 7 | Belper Town | 6 | |
| Sun, Nov 17, 2024 | Hilton Harriers | 0 | – | 6 | Long Earon United | ||
| Sun, Nov 17, 2024 | Matlock Town | 2 | – | 6 | Borrowash Victoria | ||
| Sun, Nov 17, 2024 | Wirkworth Colts | 4p | – | 4 | Ilkeston Town | 5 | |
| Quarter Final | |||||||
| Sun, Dec 15, 2024 | Wirkworth Colts | 1 | 2 | Chesterfield U23s | |||
| Sun, Dec 15, 2024 | Belper Town | 0 | 13 | Derby County U21s | |||
| Sun, Dec 15, 2024 | Chesterfield Ladies | 5 | 1 | Long Earon United | |||
| Sun, Dec 15, 2024 | Borrowash Victoria | 3 | 0 | Draycott Victoria | |||
| Semi Final | |||||||
| Sun, Jan 19, 2025 | Chesterfield Ladies | 3 | 2 | Derby County U21s | |||
| Sun, Jan 19, 2025 | Borrowash Victoria | 0 | 2 | Chesterfield U23s | |||
| Final | |||||||
| Sun, Mar 16, 2025 | Chesterfield Ladies | 3 | 0 | Chesterfield U23s | |||
| CHAMPIONS | |||||||
| Sun, Jun 1, 2025 | CHESTERFIELD LADIES | ||||||