 Nyorai kupfuurira kweiyi ndima - Sheffield United yakasaina Gillespie kubva kuLeeds City muna December 1912 nokuda kwe500 nokuda kwomubhadharo mukuru, ipapo 4 pavhiki. Gillespie akaita kutanga kwake paBhokisi Zuva 1911, achihwina mu 2x2 dhizaini neNewcastle United uye akatamba nguva dzose maBlades kubva panguva iyoyo zvichienda mberi. Gillespie akarambidzwa menduru yeFA Cup Winner muna 1915, paakapotsa kukunda kweUnited nekutyoka gumbo, akagamuchira mumutambo wekutanga wemwaka uchipesana neSunderland munaGunyana 1914. Mushure mekupera kweHondo Yenyika I, Gillespie akadzokera kuUnited uye akatangazve nzvimbo yake muboka rekutanga, kunyange zvazvo iye zvino achitamba basa rakawanda rakadzingwa semukati wepamberi. Achiramba achitamba nguva dzose, Gillespie akatora mutungamiri wekambani kubva kuna George Utley muna 1923 uye mumwaka mishanu inotevera akabatsira United kusvika kumakwikwi maviri eFA Cup uye pakupedzisira akakunda menduru yemukundi muna 1925. Achichengetedza chinzvimbo chake kwemakore matatu, Gillespie akatanga kudzidzisa vatambi vechidiki veUnited panguva yemwaka wa193031, asati arega kutamba pakupera kwemwaka iwoyo. 