Gillingham
1993
First Round19-09-1993GillinghamBrentford 2-17
1994
First Round18-09-1994GillinghamLambeth 1-6
1995
First Round17-09-1995GillinghamHarlow Town 3-7
1996
First Round29-09-1996Dulwich HamletGillingham 3-2
1997
First Round28-09-1997GillinghamStevenage Borough 12-0
Second Round02-11-1997Wembley Mill HillGillingham 7-1
1998
First Round27-09-1998Newport Pagnell Town / UnitedGillingham 3-4
Second Round01-11-1998Camberley TownGillingham 2-0
1999
Extra Preliminary Round12-09-1999NewhamGillingham O-W [1]
Preliminary Round26-09-1999GillinghamCroydon Postal 2-4
Walkover for Gillingham  [1]
2000
Extra Preliminary Round10-09-2000Gravesend & NorthfleetGillingham 1-11
Preliminary Round24-09-2000Redbridge WanderersGillingham 0-12
First Round29-10-2000GillinghamBedford Town Bells 5-1
Second Round19-11-2000GillinghamTottenham Hotspur 6-2
Third Round17-12-2000Brighton & Hove AlbionGillingham 3-1
2001
First Round04-11-2001GillinghamColney Heath 2-1
Second Round11-11-2001RedhillGillingham 4-1
2002
First Round03-11-2002GillinghamCrystal Palace 2-1
Second Round17-11-2002Haywood UnitedGillingham 2-3
Third Round29-12-2002GillinghamTorbay 1-3
2003
First Round26-10-2003BrentfordGillingham 5-5 [1]
Second Round09-11-2003GillinghamLewes 4-4 [2]
Third Round07-12-2003ChelseaGillingham 6-3
AET. 8-7 on penalties.  [1]
AET. 4-2 on penalties.  [2]
2004
First Round24-10-2004Dagenham & RedbridgeGillingham 1-1 [1]
Second Round14-11-2004GillinghamReading Royals 0-3
AET. 2-4 on penalties.  [1]
2005
First Round23-10-2005GillinghamLeyton Orient 1-2 [1]
AET  [1]
2006
First Round29-10-2006Gravesend & NorthfleetGillingham 2-3
Second Round12-11-2006Colchester UnitedGillingham 7-2
2007
First Round28-10-2007GillinghamIpswich Town 1-0
Second Round11-11-2007Chesham UnitedGillingham 3-3 [1]
AET. 6-5 on penalties  [1]
2009
First Round08-11-2009GillinghamOxford City 6-0
Second Round29-11-2009Enfield TownGillingham 0-3
Third Round13-12-2009GillinghamBarnet 1-4
2010
Second Round09-01-2011Ebbsfleet UnitedGillingham 0-6
Third Round06-02-2011GillinghamReading Women 3-5
2011
Second Round08-01-2012GillinghamColchester United 3-0
Third Round12-02-2012Keynsham TownGillingham 4-1
2012
Second Round06-01-2013GillinghamMilton Keynes Dons 6-1
Third Round03-02-2013Swindon TownGillingham 0-1 [1]
Fourth Round24-02-2013GillinghamNottingham Forest 2-3
AET. 0-0 at full time.  [1]
2013
Second Round12-01-2014Queens Park RangersGillingham 1-2 [1]
Third Round16-02-2014Nottingham ForestGillingham 0-1
Fourth Round16-03-2014GillinghamPreston North End 1-0
Fifth Round13-04-2014ArsenalGillingham 2-0
AET  [1]
2014
Second Round11-01-2015GillinghamPortsmouth 0-5
2015
Third Qualifying Round11-10-2015GillinghamAFC Wimbledon 7-0
Fourth Qualifying Round08-11-2015GillinghamHerne Bay 3-0
First Round06-12-2015London CorinthiansGillingham 3-4 [1]
Second Round17-01-2016Forest Green RoversGillingham 1-1 [2]
Third Round07-02-2016GillinghamTottenham Hotspur 0-1
AET  [1]
AET. 1-3 on penalties.  [2]
2016
Third Qualifying Round09-10-2016GillinghamMaidenhead United 4-0
Fourth Qualifying Round13-11-2016AylesfordGillingham 0-7
First Round04-12-2016Southampton SaintsGillingham 1-7
Second Round08-01-2017Tottenham HotspurGillingham 3-0
2017
Second Round03-12-2017GillinghamPlymouth Argyle 1-3 [1]
AET  [1]
2018
Second Round02-12-2018Loughborough FoxesGillingham 3-1 [1]
AET  [1]
2019
Second Round01-12-2019Billericay TownGillingham 2-1
2020
Second Round04-04-2021Crawley WaspsGillingham 2-3
Third Round11-04-2021Cheltenham TownGillingham 1-2 [1]
Fourth Round18-04-2021ArsenalGillingham 10-0
AET  [1]
2021
First Round14-11-2021Abingdon TownGillingham 1-4
Second Round28-11-2021GillinghamActonians 2-0 [1]
Third Round19-12-2021GillinghamCharlton Athletic 0-1
Abandoned after 88 minutes after injury to an Actonians player with Gillingham leading 2-0. Result stands.  [1]
2022
First Round13-11-2022Millwall LionessesGillingham 2-2 [1]
Second Round27-11-2022Dulwich HamletGillingham 1-2
Third Round11-12-2022AFC WimbledonGillingham P-P
Third Round18-12-2022AFC WimbledonGillingham P-P
Third Round08-01-2023AFC WimbledonGillingham 1-0
AET (1-1 after 90m). Gillingham Women FC won 5-4 on penalties  [1]
Chatham Town
2023
First Round12-11-2023Haywards Heath TownChatham Town 2-4
Second Round26-11-2023Chatham TownAFC Wimbledon 5-4
Third Round10-12-2023Crystal PalaceChatham Town 6-0