 Pressman anonyanya kurangarirwa semuchengeti wemagariro kwenguva refu weSheffield Wednesday, kwaakapedza mwaka gumi nemapfumbamwe, achitamba mitambo makumi mana nemasere mumakwikwi ese kusanganisira UEFA Cup. Pressman akasaina chibvumirano chake chekutanga chehunyanzvi cheOwls pazuva rake rekuzvarwa rechi18 muna 1985 uye akaita kutanga kwake kurwisa Southampton musi wa5 Gunyana 1987. Akanga atsigira Chitatu kubvira paucheche. Basa raPressman rakapotsa raparadzwa paZuva reGore Idzva ra1990 paakatambura kukuvara kwechinhambwe chebvi-ligament chakamubvisa kwemwedzi inopfuura misere. Akanga asina rombo rakanaka kuti asatambe mu 1991 League Cup Final kukunda Manchester United, sezvo akanga atamba mumutambo wose wemakwikwi gore iroro pamwe chete nenhamba yakawanda yemitambo yemakwikwi kusvikira kumativi ekupedzisira ekupedzisira apo akatsiviwa nemuchengeti wepamusoro uye mutungamiri weChitatu weChitatu Chris Turner. Pressman akanga ari pabhenji revatsinhanisi pamamwe magumo matatu eWembley, ose muna 1993; League Cup Final, FA CupFinal uye FA Cup Final replay, zvose zvinopesana neArsenal uye zvichikonzera kukundwa mumakwikwi ose eChitatu. 