Ashdown Rangers
2003
First Qualifying Round07-09-2003Plymouth Oak VillaAshdown Rangers 7-3
2004
First Qualifying Round05-09-2004Ashdown RangersSouthampton 11-2
Second Qualifying Round26-09-2004Ashdown RangersAldershot Town 3-2
First Round31-10-2004Plymouth ArgyleAshdown Rangers 9-1
Poole Town
2005
First Qualifying Round11-09-2005AFC BournemouthPoole Town 5-1
2006
First Qualifying Round24-09-2006Barnstaple TownPoole Town 2-3
Second Qualifying Round08-10-2006Poole TownAlphington 3-1
First Round29-10-2006Frome TownPoole Town 6-1
2007
First Qualifying Round16-09-2007Poole TownAlphington 5-2
Second Qualifying Round30-09-2007Ilminster TownPoole Town 0-3
Third Qualifying Round07-10-2007Poole TownOxford City 0-6
2008
Preliminary Round07-09-2008Poole TownWeymouth 0-5
2009
First Qualifying Round27-09-2009Poole TownKeynsham Town Development 0-6
2010
Second Qualifying Round24-10-2010Ilminster TownPoole Town 3-1
2011
First Qualifying Round02-10-2011Aldershot TownPoole Town 2-0
2012
First Qualifying Round30-09-2012Fleet TownPoole Town 0-5
Second Qualifying Round14-10-2012Swindon SpitfiresPoole Town 3-4 [1]
Third Qualifying Round11-11-2012Poole TownSwindon Town 1-9
AET  [1]
2013
First Qualifying Round22-09-2013Poole TownFleet Town 6-1
Second Qualifying Round06-10-2013Truro CityPoole Town 4-0
2014
Preliminary Round07-09-2014Poole TownAldershot Town 4-0
First Qualifying Round28-09-2014Poole TownBasingstoke Town 4-3 [1]
Second Qualifying Round12-10-2014Poole TownOxford City 1-2 [2]
AET  [1]
AET  [2]
2015
Second Qualifying Round27-09-2015New ForestPoole Town 0-12
Third Qualifying Round11-10-2015Chichester CityPoole Town 7-1
2016
Second Qualifying Round18-09-2016Warsash WaspsPoole Town 1-2
Third Qualifying Round09-10-2016Poole TownAEK-BOCO 3-0
Fourth Qualifying Round13-11-2016BrislingtonPoole Town 8-0
2017
Third Qualifying Round08-10-2017Poole TownPlymouth Argyle 2-5
2018
Second Qualifying Round23-09-2018Poole TownFrampton Rangers 3-1
Third Qualifying Round07-10-2018EastleighPoole Town 1-2
First Round11-11-2018Poole TownSouthampton FC Women 0-3
2019
Second Qualifying Round06-10-2019Winchester City FlyersPoole Town 2-3
Third Qualifying Round27-10-2019Southampton FC WomenPoole Town 11-0
2020
Second Qualifying Round18-10-2020Ilminster TownPoole Town 4-1
2021
Third Qualifying Round24-10-2021Poole TownTorquay United 0-6
2022
Second Qualifying Round02-10-2022Widbrook UnitedPoole Town 2-7
Third Qualifying Round23-10-2022Poole TownWeymouth 3-1 [1]
Third Qualifying Round30-10-2022Poole TownWeymouth 0-2
Abandoned after 80 minutes  [1]
2023
First Qualifying Round10-09-2023United Services PortsmouthPoole Town 3-3 [1]
United Services won 5-3 on penalties  [1]