 Nyorai kupfuurira kweiyi ndima - Akasaina nokuda kwaVaDons muna 1984 uye akaita kutanga kwake paZuva reGore Idzva 1985 kurwisana naOldham Athletic. Pakutanga kwebasa rake pakirabhu, aive nechikwereti paPorin Pallotoverit neKoparit muFinland asati azvisimbisa semunhu wenguva dzose muWimbledon. Akaenderera mberi nekuita 138 makwikwi emakwikwi ekirabhu, achiwana zvibodzwa makumi maviri nezvitanhatu sezvo vakazvisimbisa sekirabhu yeFirst Division uye vari nhengo dzekutanga dzeFA Premier League nyowani muna 1992. Mwaka wake wakanakisa yaive mwaka wa1986-87, kwaakatamba ka23 muligi uye akarova zvibodzwa zvisere mumwaka wavo wekutanga sekirabhu yeFirst Division, achipedza chinzvimbo chinoshamisa chechitanhatu uye achitotungamira tafura kutanga kwaGunyana. Chinhu chikuru chebudiriro inoshamisa yeWimbledon chakauya pakupera kwemwaka wa198788 pavakasvika mufainari yeFA Cupuye vakakwanisa kukunda Liverpool 1-0. Zvisinei, gumbo rakaputsika raireva kuti Fairweather akanga asiri muchikwata chemutambo iwoyo, kunyange zvazvo akaonekwa ka21 muligi asati akuvara uye akarova zvibodzwa zvina kuti abatsire kuwana nzvimbo yechinomwe. Pakupera kwenguva yake kuWimbledon, akanga ava murume akanganwika wekirabhu, achitadza kuita chikwata chimwe chete mumwaka wake wokupedzisira uye akatamba ka11 chete pamwe chete mumwaka miviri isati yasvika. 