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16 out. 2021|14:00FimSouthend United4 - 1Chertsey TownFA CupRoots Hall StadiumVictoria Avenue, PrittlewellSouthend-on-SeaGlobal16 out. 2021|14:00FA CupRoots Hall StadiumVictoria Avenue, PrittlewellSouthend-on-SeaGlobalFim
6 nov. 2021|15:00FimChesterfield3 - 1Southend UnitedFA CupTechnique Stadium1866 Sheffield Road, Whittington MoorChesterfieldGlobal6 nov. 2021|15:00FA CupTechnique Stadium1866 Sheffield Road, Whittington MoorChesterfieldGlobalFim
15 out. 2022|14:00FimWoking2 - 1Southend UnitedFA CupThe Laithwaite Community StadiumKingfield RoadWokingGlobal15 out. 2022|14:00FA CupThe Laithwaite Community StadiumKingfield RoadWokingGlobalFim
14 out. 2023|14:00FimYeovil Town2 - 0Southend UnitedFA CupHuish Park StadiumLufton Way, LuftonYeovilGlobal14 out. 2023|14:00FA CupHuish Park StadiumLufton Way, LuftonYeovilGlobalFim
12 out. 2024|14:00FimEastleigh0 - 1Southend UnitedFA CupSilverlake StadiumStoneham LaneEastleighGlobal12 out. 2024|14:00FA CupSilverlake StadiumStoneham LaneEastleighGlobalFim
2 nov. 2024|15:00Fim (Pror.)Southend United3 - 4Charlton AthleticFA CupRoots Hall StadiumVictoria Avenue, PrittlewellSouthend-on-SeaGlobal2 nov. 2024|15:00FA CupRoots Hall StadiumVictoria Avenue, PrittlewellSouthend-on-SeaGlobalFim (Pror.)
11 out. 2025|14:00FimSouthend United4 - 1Folkestone InvictaFA CupRoots Hall StadiumVictoria Avenue, PrittlewellSouthend-on-SeaGlobal11 out. 2025|14:00FA CupRoots Hall StadiumVictoria Avenue, PrittlewellSouthend-on-SeaGlobalFim
1 nov. 2025|15:00FimWealdstone1 - 0Southend UnitedFA CupGrosvenor ValeGrosvenor ValeRuislipGlobal1 nov. 2025|15:00FA CupGrosvenor ValeGrosvenor ValeRuislipGlobalFim
17 out. 2026|14:00FimSouthend United1 - 2BerkhamstedFA CupRoots Hall StadiumVictoria Avenue, PrittlewellSouthend-on-SeaGlobal17 out. 2026|14:00FA CupRoots Hall StadiumVictoria Avenue, PrittlewellSouthend-on-SeaGlobalFim