Tue 3rd December
- Milton Keynes Dons
- 19:45
- Chesterfield
- Match Preview
League 2, Sky Sports+ (18:45)
Thu 26th December
- Fleetwood Town
- 15:00
- Chesterfield
- Match Preview
League 2, Sky Sports+ (14:00)
Wed 1st January
- Chesterfield
- 15:00
- Milton Keynes Dons
- Match Preview
League 2, Sky Sports+ (14:00)
Sat 11th January
- Salford City
- 12:30
- Chesterfield
- Match Preview
League 2, Sky Sports+ (12:30)
