Chelmsford City
1990
First Round - Group 4Bye
Second Round - Group 404-11-1990SouthendChelmsford City 2-0 
1991
First Round - Group 215-09-1991BecclesChelmsford City 4-6 
Second Round - Group 206-10-1991Leyton OrientChelmsford City 6-2 
1992
First Round - Group 813-09-1992Chelmsford CityColchester United 1-2 
1996
First Round29-09-1996Chelmsford CityLeatherhead 2-1 
Second Round03-11-1996Abbey RangersChelmsford City 4-5 
Third Round01-12-1996Chelmsford CityBarnet 1-1 [1]
Third Round08-12-1996BarnetChelmsford City 2-2 [2]
Fourth Round19-01-1997Chelmsford CityHuddersfield Town 2-5 
AET  [1]
AET. Chelmsford won 5-3 on penalties  [2]
1997
First Round28-09-1997Chelmsford CityAylesbury Stocklake 3-0 
Second Round02-11-1997LangfordChelmsford City 1-1 [1]
Second Round09-11-1997Chelmsford CityLangford 0-4 
After Extra Time  [1]
1998
First Round27-09-1998Chelmsford CityRedhill W/O [1]
Second Round01-11-1998Chelmsford CityWatford 1-1 [2]
Second Round08-11-1998WatfordChelmsford City 5-1 
Walkover for Chelmsford  [1]
AET  [2]
2000
First Round29-10-2000SloughChelmsford City 0-4 
Second Round19-11-2000StowmarketChelmsford City 3-0 
2001
First Round28-10-2001Chelmsford CityCharlton 3-2 [1]
Second Round11-11-2001HamptonChelmsford City 3-2 
AET  [1]
2003
First Qualifying Round07-09-2003Chelmsford CityCaversham 5-6 
2004
First Qualifying Round05-09-2004Haringey BoroughChelmsford City 1-7 
Second Qualifying Round26-09-2004LordswoodChelmsford City 3-1 
2005
First Qualifying Round11-09-2005Chelmsford CityAbbey Rangers 3-2 
Second Qualifying Round25-09-2005Chelmsford CityNewport Pagnell Town 9-0 
First Round23-10-2005Dagenham & RedbridgeChelmsford City 5-2 
2006
Preliminary Round10-09-2006Colchester TownChelmsford City 1-6 
First Qualifying Round24-09-2006Brentwood TownChelmsford City 1-7 
Second Qualifying Round08-10-2006GarstonChelmsford City 6-0 
2007
First Qualifying Round16-09-2007Billericay TownChelmsford City 2-0 
2009
First Qualifying Round27-09-2009Runwell HospitalChelmsford City 2-5 
Second Qualifying Round11-10-2009Brentwood TownChelmsford City 1-4 
Third Qualifying Round25-10-2009Woodbridge TownChelmsford City 3-3 [1]
AET. 8-7 on penalties.  [1]
2010
Second Qualifying Round24-10-2010Chelmsford CityRoyston Town W/O [1]
Third Qualifying Round14-11-2010Chelmsford CityBarking 2-2 [2]
First Round12-12-2010Tottenham HotspurChelmsford City 5-0 
Walkover for Chelmsford City.  [1]
AET. 6-5 on penalties.  [2]
2011
First Qualifying Round02-10-2011Wymondham TownChelmsford City 0-8 
Second Qualifying Round23-10-2011Chelmsford CityHethersett Athletic 0-7 
2012
First Qualifying Round30-09-2012Chelmsford CityFakenham Town W/O [1]
Second Qualifying Round14-10-2012Chelmsford CityC&K Basildon 2-3 
Walkover for Chelmsford City.  [1]
2016
Second Qualifying Round18-09-2016Haringey BoroughChelmsford City 12-0 
2017
First Qualifying Round03-09-2017Billericay TownChelmsford City 8-0 
2018
Preliminary Round26-08-2018Beccles TownChelmsford City 0-1 
First Qualifying Round02-09-2018Chelmsford CityAFC Sudbury 0-1 
2020
Extra Preliminary Round06-09-2020Chelmsford CityFrontiers 3-2 
Preliminary Round20-09-2020Chelmsford CityLeigh Ramblers 1-2 
2021
First Qualifying Round12-09-2021Chelmsford CityHoughton Athletic 10-0 
Second Qualifying Round03-10-2021Watford DevelopmentChelmsford City 2-5 
Third Qualifying Round24-10-2021London SeawardChelmsford City 8-0 
2022
Second Qualifying Round02-10-2022Chelmsford CityHarpenden Town 2-2 [1]
Harpenden Town won 4-3 on penalties  [1]
2023
First Qualifying Round10-09-2023Grays AthleticChelmsford City 2-1