7 nov 2020|15:00Final (Pen.)Boreham Wood2 - 2Southend UnitedFA CupMeadow ParkBroughinge RoadBorehamwoodGlobal7 nov 2020|15:00FA CupMeadow ParkBroughinge RoadBorehamwoodGlobalFinal (Pen.)
16 oct 2021|14:00FinalSouthend United4 - 1Chertsey TownFA CupRoots Hall StadiumVictoria Avenue, PrittlewellSouthend-on-SeaGlobal16 oct 2021|14:00FA CupRoots Hall StadiumVictoria Avenue, PrittlewellSouthend-on-SeaGlobalFinal
6 nov 2021|15:00FinalChesterfield3 - 1Southend UnitedFA CupTechnique Stadium1866 Sheffield Road, Whittington MoorChesterfieldGlobal6 nov 2021|15:00FA CupTechnique Stadium1866 Sheffield Road, Whittington MoorChesterfieldGlobalFinal
15 oct 2022|14:00FinalWoking2 - 1Southend UnitedFA CupThe Laithwaite Community StadiumKingfield RoadWokingGlobal15 oct 2022|14:00FA CupThe Laithwaite Community StadiumKingfield RoadWokingGlobalFinal
14 oct 2023|14:00FinalYeovil Town2 - 0Southend UnitedFA CupHuish Park StadiumLufton Way, LuftonYeovilGlobal14 oct 2023|14:00FA CupHuish Park StadiumLufton Way, LuftonYeovilGlobalFinal
12 oct 2024|14:00FinalEastleigh0 - 1Southend UnitedFA CupSilverlake StadiumStoneham LaneEastleighGlobal12 oct 2024|14:00FA CupSilverlake StadiumStoneham LaneEastleighGlobalFinal
2 nov 2024|15:00Final (Pró.)Southend United3 - 4Charlton AthleticFA CupRoots Hall StadiumVictoria Avenue, PrittlewellSouthend-on-SeaGlobal2 nov 2024|15:00FA CupRoots Hall StadiumVictoria Avenue, PrittlewellSouthend-on-SeaGlobalFinal (Pró.)
11 oct 2025|14:00FinalSouthend United4 - 1Folkestone InvictaFA CupRoots Hall StadiumVictoria Avenue, PrittlewellSouthend-on-SeaGlobal11 oct 2025|14:00FA CupRoots Hall StadiumVictoria Avenue, PrittlewellSouthend-on-SeaGlobalFinal
1 nov 2025|15:00FinalWealdstone1 - 0Southend UnitedFA CupGrosvenor ValeGrosvenor ValeRuislipGlobal1 nov 2025|15:00FA CupGrosvenor ValeGrosvenor ValeRuislipGlobalFinal
17 oct 2026|14:00FinalSouthend United1 - 2BerkhamstedFA CupRoots Hall StadiumVictoria Avenue, PrittlewellSouthend-on-SeaGlobal17 oct 2026|14:00FA CupRoots Hall StadiumVictoria Avenue, PrittlewellSouthend-on-SeaGlobalFinal
InglaterraRoots Hall Stadium
InglaterraRoots Hall StadiumInglaterraRoots Hall Stadium
