Sharley Park Spireites
1991
First Round - Group 415-09-1991Sharley Park SpireitesDerby County 6-0
Second Round - Group 406-10-1991Sharley Park SpireitesLeicester 3-2
Third Round - Group 403-11-1991Sharley Park SpireitesSpondon 0-4
Sharley Park
1992
1st Round - Group 713-09-1992Sharley ParkGrimsby 5-1
2nd Round - Group 704-10-1992Leicester CitySharley Park 3-3
2nd Round - Group 711-10-1992Sharley ParkLeicester City 3-4
Chesterfield
1993
Second Round17-10-1993ChesterfieldTNT 3-1
Third Round14-11-1993ChesterfieldBury 2-1
Fourth Round05-12-1993ChesterfieldWakefield 1-2
1994
Second Round16-10-1994ChesterfieldVilla Aztecs 2-5
1995
First Round17-09-1995Warrington TownChesterfield 1-2 [1]
Second Round15-10-1995Coventry CityChesterfield 2-1
AET  [1]
1996
First Round29-09-1996SunderlandChesterfield 3-4 [1]
Second Round03-11-1996ChesterfieldBangor City 1-3
AET  [1]
1997
First Round28-09-1997Blackburn RoversChesterfield 3-2
1998
First Round27-09-1998ChesterfieldMelton Mowbray 9-0
Second Round01-11-1998Coventry CityChesterfield 2-1
1999
First Round10-10-1999Peterborough UnitedChesterfield 2-1
2000
First Round29-10-2000ChesterfieldKettering Amazons 8-2
Second Round12-11-2000Mansfield TownChesterfield 5-3 [1]
AET  [1]
2001
First Round28-10-2001Shrewsbury TownChesterfield 1-4
Second Round11-11-2001ChesterfieldLeicester City 1-3
2002
First Round27-10-2002Blackburn RoversChesterfield 6-0
2003
Third Round07-12-2003ChesterfieldManchester United 1-2
2004
First Round24-10-2004Lichfield DiamondsChesterfield 3-4
Second Round14-11-2004ChesterfieldGarswood Saints 2-1
Third Round05-12-2004Leafield AthleticChesterfield 3-2
2005
First Round23-10-2005ChesterfieldShrewsbury Town 2-1
Second Round13-11-2005ChesterfieldNorthampton Town 0-2
2006
First Round29-10-2006ChesterfieldPenrith AFC 2-3
2007
1st Qualifying Round16-09-2007ChesterfieldFriar Lane & Epworth O-W [1]
Walkover for Friar Lane & Epworth.  [1]
2018
Preliminary Round26-08-2018Hepworth UnitedChesterfield 0-4
1st Qualifying Round02-09-2018ChesterfieldYorkshire Amateur AFC 4-0
2nd Qualifying Round30-09-2018ChesterfieldBurton Albion 1-0
3rd Qualifying Round07-10-2018ChesterfieldStockport County 0-6
2019
Preliminary Round01-09-2019Lutterworth AthleticChesterfield 0-12
1st Qualifying Round22-09-2019ChesterfieldCookley Sports 2-0
2nd Qualifying Round06-10-2019ChesterfieldBedworth United 1-3
2021
2nd Qualifying Round03-10-2021Grimsby BoroughChesterfield 1-3
3rd Qualifying Round24-10-2021ChesterfieldBedworth United 1-2
2022
2nd Qualifying Round02-10-2022ChesterfieldPocklington Town AFC 10-0
3rd Qualifying Round30-10-2022Wem TownChesterfield 1-0
2023
2nd Qualifying Round01-10-2023HandsworthChesterfield 1-2
3rd Qualifying Round22-10-2023ChesterfieldNottingham Trent University 3-1
First Round12-11-2023Sutton Coldfield TownChesterfield 8-0
2024
2nd Qualifying Round22-09-2024Ilkley Town AFCChesterfield 0-3
3rd Qualifying Round13-10-2024ChesterfieldBradford City 1-2