Cheltenham YMCA
1993
First Round19-09-1993Cheltenham YMCATruro City 3-3 [1]
First Round26-09-1993Truro CityCheltenham YMCA 4-4 [2]
AET  [1]
AET. Pens 2-0  [2]
1994
First Round18-09-1994Plymouth PilgrimsCheltenham YMCA 4-2 
1995
First Round17-09-1995Cheltenham YMCAFreeway 12-1 
Second Round15-10-1995Cheltenham YMCABarry Town 2-2 
Second Round22-10-1995Barry TownCheltenham YMCA 2-1 
Cheltenham Town
2000
First Round19-11-2000Saltash PilgrimsCheltenham Town 1-4 
Second Round26-11-2000Cheltenham TownPortsmouth 3-2 
Third Round17-12-2000Bristol RoversCheltenham Town 7-0 
2008
Preliminary Round14-09-2008Cheltenham TownNewbury 5-0 
1st Qualifying Round28-09-2008Stoke Lane AthleticCheltenham Town 3-6 
2nd Qualifying Round12-10-2008Cheltenham TownLaunton 3-1 
3rd Qualifying Round26-10-2008Wycombe WanderersCheltenham Town 3-3 [1]
First RoundBye
Second Round23-11-2008Forest Green RoversCheltenham Town 2-0 
AET. 3-4 on penalties.  [1]
2009
1st Qualifying Round27-09-2009Bracknell TownCheltenham Town 3-0 
2010
2nd Qualifying Round24-10-2010Banbury UnitedCheltenham Town 0-4 
3rd Qualifying Round14-11-2010Bracknell TownCheltenham Town 2-0 
2011
1st Qualifying Round02-10-2011Cheltenham TownIlminster Town 4-2 [1]
2nd Qualifying Round23-10-2011Cheltenham TownBridgwater Town 0-3 
AET  [1]
2012
1st Qualifying Round30-09-2012Falmouth TownCheltenham Town 8-2 
2013
1st Qualifying Round22-09-2013Cheltenham TownPen Mill 9-0 
2nd Qualifying Round06-10-2013Cheltenham TownIlminster Town 2-1 
3rd Qualifying Round03-11-2013Swindon SpitfiresCheltenham Town 3-2 
2014
3rd Qualifying Round02-11-2014Cheltenham TownSt Nicholas 2-1 
First Round07-12-2014Cheltenham TownExeter City 1-2 
2015
3rd Qualifying Round11-10-2015Keynsham TownCheltenham Town 6-2 
2016
3rd Qualifying Round09-10-2016Larkhall AthleticCheltenham Town 9-1 
2017
3rd Qualifying Round08-10-2017Cheltenham TownSouthampton Saints 1-4 
2018
2nd Qualifying Round23-09-2018Cheltenham TownBrislington 4-1 
3rd Qualifying Round07-10-2018Cheltenham TownExeter City 1-0 
First Round11-11-2018Buckland AthleticCheltenham Town 2-0 
2019
2nd Qualifying Round06-10-2019Cheltenham TownBrislington 5-0 
3rd Qualifying Round03-11-2019Cheltenham TownExeter City 4-3 
First Round17-11-2019Cheltenham TownLeyton Orient 0-1 
2020
2nd Qualifying Round18-10-2020Cheltenham TownBrislington 3-0 
3rd Qualifying Round01-11-2020Cheltenham TownPortishead Town 3-1 
First Round13-12-2020Exeter CityCheltenham Town 1-1 [1]
Second Round04-04-2021PortsmouthCheltenham Town 2-0 [2]
Third Round11-04-2021Cheltenham TownGillingham 1-2 [3]
AET. Pens 3-4  [1]
AET. Awarded to Cheltenham Town  [2]
AET  [3]
2021
3rd Qualifying Round24-10-2021Cheltenham TownLarkhall Athletic 3-1 
First Round14-11-2021Cheltenham TownLiskeard Athletic 4-0 
Second Round28-11-2021Cheltenham TownSouthampton 3-3 [1]
After Extra Time. 5-6 on penalties.  [1]
2022
First Round13-11-2022Plymouth ArgyleCheltenham Town 4-2 
2023
First Round12-11-2023Cardiff CityCheltenham Town 0-3 
Second Round26-11-2023Cheltenham TownExeter City 3-2 
Third Round10-12-2023Cheltenham TownReading Women 0-4 
2024
First Round03-11-2024Cheltenham TownYeovil Town 7-0 
Second Round24-11-2024Cheltenham TownMoneyfields 2-1 
Third Round08-12-2024Cheltenham TownNorwich City 2-1 [1]
Fourth Round12-01-2025Cheltenham TownWolverhampton Wanderers 0-2 
After Extra Time. 1-1 after 90 minutes.  [1]