21 Aug 2021|14:00EndstandMarske United7 - 0Pickering Town CFCFA CupGER StadiumMount Pleasant AvenueMarske-by-the-SeaGlobal21 Aug 2021|14:00FA CupGER StadiumMount Pleasant AvenueMarske-by-the-SeaGlobalEndstand
6 Aug 2022|14:00EndstandHeaton Stannington1 - 0Pickering Town CFCFA CupGrounsell ParkGrounsell ParkNewcastle upon TyneGlobal6 Aug 2022|14:00FA CupGrounsell ParkGrounsell ParkNewcastle upon TyneGlobalEndstand
3 Aug 2024|14:00UnbekanntPenrith AFCVSPickering Town CFCFA CupThe World Group StadiumThe World Group StadiumPenrithGlobal3 Aug 2024|14:00FA CupThe World Group StadiumThe World Group StadiumPenrithGlobalUnbekannt
1 Aug 2025|18:45EndstandPickering Town CFC3 - 2Penrith AFCFA CupMill LaneMill LanePickeringGlobal1 Aug 2025|18:45FA CupMill LaneMill LanePickeringGlobalEndstand
15 Aug 2025|18:45EndstandPickering Town CFC0 - 0Easington CollieryFA CupMill LaneMill LanePickeringGlobal15 Aug 2025|18:45FA CupMill LaneMill LanePickeringGlobalEndstand
20 Aug 2025|18:45EndstandEasington Colliery0 - 2Pickering Town CFCFA Cup20 Aug 2025|18:45FA CupEndstand
29 Aug 2025|19:00EndstandPickering Town CFC5 - 2Redcar AthleticFA CupMill LaneMill LanePickeringGlobal29 Aug 2025|19:00FA CupMill LaneMill LanePickeringGlobalEndstand
13 Sep 2025|11:30EndstandPickering Town CFC0 - 2Runcorn LinnetsFA CupMill LaneMill LanePickeringGlobal13 Sep 2025|11:30FA CupMill LaneMill LanePickeringGlobalEndstand
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