 Nyorai kupfuurira kweiyi ndima - Mukutanga kwema1930, Cowan akava kaputeni weManchester City, achitevera Jimmy McMullan. Mukati mokutungamira kwake kirabhu yakasvika mamwe maviri FA Cup Finals. Yokutanga yacho yaiva muna 1933, vachirwisa Everton. Munguva yemutambo Cowan akanga achirwisana naKaputeni weEverton Dixie Dean. Vatambi vose vari vaviri vakanga vakakurumbira nokuda kwokugona kwavo kutungamirira. Matt Busby akataura kuti Cowan aigona kutungamira bhora kure sekuti vazhinji vedu taigona kurirova, asi Dean akakunda muhondo yemhepo, achihwina zvibodzwa zvechipiri zveEverton nemusoro. Daily Mail yakataura kuti kuvapo kwaDean kwakapa Cowan dambudziko: Akanga akavhiringidzika pakati pekutsunga kusasiya Dean uye chido chekubatsira mberi kwake. Akaputsika pakati pezviviri. Everton yakanga iri 3-0 vakundi, asi apo Cowan akagamuchira menduru yake yemumhanyi kubva kuDuke weYork, akataura kuti aizodzoka gore rinouya kuzokunda. Sezvakanga zvataurwa naCowan, City yakadzokera kuWembley gore rakatevera racho. Mumutambo wokupedzisira weFA Cup ya1934, Cowan akava wokutanga uye saka kure chete Manchester City mutambi kumiririra kirabhu muna nhatu FA Cup yokupedzisira. Akatungamirira City kukunda Portsmouth 2-1. Somutungamiriri wechikwata Cowan aiva nebasa guru rokukurudzira vamwe vake vatambi uye kuronga mitambo. Izvi zvakanga zvakajairika kumutungamiriri wenguva yake, sezvo vatungamiri venguva yacho vaive vatungamiri vaive vasina ruzivo rwakawanda mukudzidzisa uye maitiro. 